2-Hydroxyphenyltriphenylphosphonium bromide → Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate

HRID 1927427Notes

Reaction equation

HRID 1927427 reaction equation
[CH2:1]([Li])CCC.[Br-].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([CH:52]=O)[CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)#[N:34]>CCCCCC.C1COCC1>[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39](/[CH:52]=[CH:1]/[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[OH:7])[CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)#[N:34]

Participants

6

Reactant 3

HCID 573460052-Hydroxyphenyltriphenylphosphonium bromideHCID 57831357Methyl 4-(7-cyano-3-formylheptyl)benzoateHCID 178418339Butyllithium

Product 1

HCID 57831335Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

9.07 ml (14.52 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added dropwise to a suspension of 3.26 g (7.26 mmol) of 2-hydroxyphenyltriphenylphosphonium bromide in 40 ml of dry THF at 0° C., and the mixture is stirred for 5 minutes. Then, at this temperature, a solution of 1.49 g (5.19 mmol) of methyl 4-(7-cyano-3-formylheptyl)benzoate in 10 ml of dry THF is slowly added dropwise. The reaction mixture is stirred at 0° C. for 10 minutes. The cooling is then removed, and the reaction solution is stirred at room temperature for 10 minutes and then mixed with silica gel and concentrated to dryness. The resulting residue is purified directly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→1:5). 1.71 g (75% purity, 3.40 mmol, 65% of theory) of an oil are obtained.

Workup

  1. stirringThe reaction mixture is stirred at 0° C. for 10 minutes
  2. customThe cooling is then removed
  3. stirringthe reaction solution is stirred at room temperature for 10 minutes
  4. additionmixed with silica gel
  5. concentrationconcentrated to dryness
  6. customThe resulting residue is purified directly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:2→1:5)
  7. custom1.71 g (75% purity, 3.40 mmol, 65% of theory) of an oil are obtained

Sources & evidence

ORD record
ord-f4281a737506442ebcb53343d17249b2
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

Loading…