Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-ethyl 3-(4-(benzyloxy)-2-isopropoxyphenyl)acrylate

HRID 445862Notes

Reaction equation

HRID 445862 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:26]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 106357444-(Benzyloxy)-2-isopropoxybenzaldehyde

Product 1

HCID 58566403(E)-ethyl 3-(4-(benzyloxy)-2-isopropoxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(benzyloxy)-2-isopropoxybenzaldehyde (698) (480 mg, 1.776 mmol) and (carbethoxymethylene)triphenylphosphorane (1.1 eq.) in toluene was heated at 100° C. overnight. The reaction was cooled to room temperature and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford (E)-ethyl 3-(4-(benzyloxy)-2-isopropoxyphenyl)acrylate (699).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5af9a1c93e6846829084c5925533497b
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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