Benzyl acrylate → Benzyl 6-(4-bromophenyl)-7-hydroxyhept-2-enoate

HRID 515388Notes

Reaction equation

HRID 515388 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH:13]=[CH2:14])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:15]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:18])C=C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:9][OH:10])[CH2:11][CH2:12][CH:13]=[CH:14][C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 75617Benzyl acrylateHCID 571619042-(4-Bromophenyl)hex-5-en-1-ol

Product 1

HCID 123921660Benzyl 6-(4-bromophenyl)-7-hydroxyhept-2-enoateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a degassed solution of 2-(4-bromophenyl)hex-5-en-1-ol (108 mg, 0.423 mmol) in DCM (5 ml) at room temperature was added benzyl acrylate (0.191 ml, 1.270 mmol) and Grubbsll (35.9 mg, 0.042 mmol) and the mixture was stirred at 40° C. for 30 min. The mixture was concentrated and the residue was purified by flash chromatography (5 to 40% Acetone/Heptane) to give the title compound 130 mg (yield 79%). MS (ESI) m/z 490.4 (M+1). Retention time 1.49 min (condition A).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography (5 to 40% Acetone/Heptane)

Sources & evidence

ORD record
ord-907b5f5d49e94e1cb81a671660b8a55f
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

Loading…