3-Phenylprop-2-En-1-Ol → [(1Z)-3-Chloro-1-propen-1-yl]benzene

HRID 1867252Notes

Reaction equation

HRID 1867252 reaction equation
[CH2:1](O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1C(C)=CC(C)=CC=1C.[Cl-].[Li+].CS([Cl:26])(=O)=O>CN(C=O)C.CCOCC>[CH2:1]([Cl:26])/[CH:2]=[CH:3]\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 3083-Phenylprop-2-En-1-OlHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium Chloride

Product 1

HCID 10997235[(1Z)-3-Chloro-1-propen-1-yl]benzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the cinnamyl alcohol (1-1) (17.8 g, 133 mmol; Fukuda, et al., Tetrahedron 55, 1999, pp 649-664) in DMF (75 mL) was treated with collidine (35.1 mL, 32.2 g, 266 mmol), lithium chloride (11.2 g, 266 mmol), and methanesulfonyl chloride (20.7 mL, 30.6 g, 173 mmol) at room temperature. After stirring for 12 h, the reaction was diluted with Et2O (300 mL) and washed with water, satd aq NH4Cl, and brine. The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, 5% EtOAc/hexanes) to give allyl chloride (1-2) as a colorless oil. 1NMR (500 MHz, CDCl3) δ 7.40 (m, 2H), 7.32 (m, 3H), 6.68 (d, J=11 hz, 1H), 5.94 (m, 1H), 4.30 (m, 2H) ppm.

Workup

  1. washwashed with water
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (SiO2, 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b819b092bdc34182a0cf85804c6a6c55
Source dataset
uspto-grants-2009_12
Patent number
US07632833B2

Reaction notes

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