Water → HCID 57831366, compound

HRID 1672619Notes

Reaction equation

HRID 1672619 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:56]=O)[CH2:45][C:46]2[CH:55]=[CH:54][C:49]([C:50]([O:52][CH3:53])=[O:51])=[CH:48][CH:47]=2)=[CH:38][CH:37]=1)#[N:35].O>CCCCCC.C1COCC1>[C:34]([C:36]1[CH:37]=[CH:38][C:39]([CH2:42][CH2:43][CH:44](/[CH:56]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][C:46]2[CH:47]=[CH:48][C:49]([C:50]([O:52][CH3:53])=[O:51])=[CH:54][CH:55]=2)=[CH:40][CH:41]=1)#[N:35]

Participants

7

Reactant 4

HCID 962WaterHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57831348Methyl 4-[4-(4-cyanophenyl)-2-formylbutyl]benzoateHCID 178418339Butyllithium

Product 1

HCID 57831366HCID 57831366, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

9.39 ml (15.02 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 2.459 g (5.36 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 65 ml of anhydrous THF at 0° C. Then, at this temperature, 1.744 g (5.36 mmol) of methyl 4-[4-(4-cyanophenyl)-2-formylbutyl]benzoate from Example 16A, dissolved in 65 ml of THF, are slowly metered in. After warming to room temperature, the reaction solution is stirred for 12 hours and then, after addition of some water, concentrated to dryness. The resulting 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 crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 1.44 g (3.50 mmol, 65% 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 crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-fe0ec376f56c49a581be011264fa4541
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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