HCID 563558, compound → HCID 13564633, compound

HRID 1285535Notes

Reaction equation

HRID 1285535 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].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:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:13][CH:12]=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 202495094-[4-(Hexyloxy)phenyl]-2-butanoneHCID 45051747Lithium diisopropylamine

Product 1

HCID 13564633HCID 13564633, compound

Procedure

In a manner similar to Example 3, 2.48 g (10 mmol) of 4-(4-hexyloxyphenyl)-butan-2-one was treated with 15 mmol of lithium diisopropylamine, followed by 3 g (12 mmol) of 3-(4-benzyloxyphenyl)-propan-1-al to give, after purification (silica gel dry column, hexane: ethyl acetate, 2:1), 0.7 g of the title compound pound as a pale yellow oil. MS(EI): 488 (m+), 470 (m+ -H2O) Using the method described hereinabove, the following examples further illustrate the invention:

Workup

  1. customto give
  2. customafter purification (silica gel dry column, hexane: ethyl acetate, 2:1), 0.7 g of the title compound pound as a pale yellow oil

Sources & evidence

ORD record
ord-d9e085880a6842068d399443f6aaa8ec
Source dataset
uspto-grants-1986_01
Patent number
US04567279

Reaction notes

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