Water → Ethyl E-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate

HRID 1672675Notes

Reaction equation

HRID 1672675 reaction equation
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH:44]([CH:54]=O)[CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:38][CH:37]=1)#[N:35].O>CCCCCC.C1COCC1>[C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH:44](/[CH:54]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:38][CH:37]=1)#[N:35]

Participants

7

Reactant 4

HCID 962WaterHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57831367Ethyl 8-(4-cyanophenyl)-6-formyloctanoateHCID 178418339Butyllithium

Product 1

HCID 57831338Ethyl E-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoateYield 64.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

15.91 ml (25.45 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 5.066 g (10.91 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 38 ml of anhydrous THF at 0° C. Then, at this temperature, 2.740 g (9.09 mmol) of ethyl 8-(4-cyanophenyl)-6-formyloctanoate from Example 86A, dissolved in 38 ml of THF, are slowly metered in. After the reaction solution has been warmed to room temperature it is stirred for 12 hours and, after addition of some water, concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 2.30 g (5.88 mmol, 63% yield) of a colorless solid are obtained.

Workup

  1. concentrationconcentrated to dryness
  2. washwashed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe solvent is concentrated to dryness
  6. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1)

Sources & evidence

ORD record
ord-a5018439b4154f40b0a5691879db1584
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…