alpha-Hydroxymethylen-verlängerte Aldehyde durch schonende Reduktion von Cyanhydrinen

The OH group in cyanohydrins RR1C(OH)CN [R = Me2CH, R1 = H; R = R1 = Me; RR1 = (CH2)4, (CH2)5] was protected with EtOCH:CH2 to give RR1C(CN)OCHMeOEt, which were then reduced by NaAlH2(OCH2CH2OMe)2 to RR1C(CHO)OCHMeOEt (I) (53-70%), which were hydrolyzed with dil. acid to RR1C(OH)CHO (these compds. dimerize readily). I reacted with Ph3P+MeBr- and BuLi to give RR1C(CH:CH)OCHMeOEt and with LiAlH4 to give RR1C(CH2OH)OCHMeOEt. Reaction of PhCH(CN)OCHMeOEt with PhMgBr, followed by hydrolysis gave benzoin, and redn. with LiAlH4 in the presence of BzCl gave PhCH(OH)CH2NHBz. [on SciFinder (R)]


Published in:
Helvetica Chimica Acta, 61, 5, 1903-11
Year:
1978
Keywords:
Note:
CAN 89:146361
23-14
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
written in German.
75-86-5; 931-97-5; 5117-85-1; 15344-34-0 Role: PROC (Process) (acetal formation of, with Et vinyl ether); 109-92-2 Role: PROC (Process) (acetal formation of, with cyanohydrins); 67755-91-3P; 67755-92-4P; 67755-93-5P; 67755-94-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 53411-98-6P; 67755-86-6P; 67755-87-7P; 67755-88-8P; 67755-89-9P; 67755-90-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 119-53-9P; 3487-44-3P; 34119-82-9P; 38968-69-3P; 67755-95-7P; 67755-96-8P; 67755-97-9P; 67755-98-0P; 67755-99-1P; 67756-00-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 19493-09-5 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with a-hydroxy aldehyde acetals)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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