Ammonium Chloride → Ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate

HRID 1672696Notes

Reaction equation

HRID 1672696 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:54]=[CH:53][C:39]([CH2:40][CH:41]([CH:51]=O)[CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:38][CH:37]=1)#[N:35].[Cl-].[NH4+]>CCCCCC.C1COCC1>[C:34]([C:36]1[CH:54]=[CH:53][C:39]([CH2:40][CH:41](/[CH:51]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:38][CH:37]=1)#[N:35]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 22560992Ethyl 6-(4-cyanobenzyl)-7-oxoheptanoateHCID 178418339Butyllithium

Product 1

HCID 57831344Ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoateYield 32.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

15.98 ml (39.95 mmol) of a 2.5 M solution of n-butyllithium in hexane are slowly added to a solution of 6.411 g (14.27 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 300 ml of anhydrous THF at 0° C. Then, at this temperature, 4.1 g (14.27 mmol) of ethyl 6-(4-cyanobenzyl)-7-oxoheptanoate from Example 111A are slowly metered in. After warming to room temperature, the reaction solution is stirred for 12 hours and then mixed with saturated ammonium chloride solution and 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 4:1). 1.75 g (4.64 mmol, 32% 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 4:1)

Sources & evidence

ORD record
ord-dccc92ab4f5341aeb74ddfe76d1a23a3
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…