HCID 563558, compound → HCID 13564632, compound

HRID 1285534Notes

Reaction equation

HRID 1285534 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[O:9][Si](C)(C)C.C(NC(C)C)(C)C.[Li].[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH:43]=[O:44])=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([O:34][C:35]1[CH:36]=[CH:37][C:38]([CH2:41][CH2:42][CH:43]([OH:44])[CH2:17][C:16](=[O:18])[CH2:15][CH2:14][C:5]2[CH:6]=[CH:7][C:8]([OH:9])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:39][CH:40]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 563558HCID 563558, compoundHCID 135646264-{3-Methoxy-4-[(trimethylsilyl)oxy]phenyl}butan-2-oneHCID 45051747Lithium diisopropylamine

Product 1

HCID 13564632HCID 13564632, compoundYield 11.5%

Procedure

In a manner similar to Example 3, 2.2 g (10 mmol) of 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one was treated with 10 mmol of lithium diisopropylamine, followed by 3 g (12 mmol) of 3-(4-benzyloxyphenyl)propan-1-al. Purification of reaction mixture by dry column chromatography (silica gel, hexane: ethyl acetate, 2:1) gave 0.5 g of the desired product as a pale yellow oil. MS(EI):434.

Workup

  1. customPurification of reaction mixture
  2. dry with materialby dry column chromatography (silica gel, hexane: ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-aaa589e54eb44023abef8005f81bbb44
Source dataset
uspto-grants-1986_01
Patent number
US04567279

Reaction notes

Loading…