Thionyl Chloride → 3-[Chloro(cyclopentyl)methyl]-2-methyl-5-phenylfuran

HRID 1877066Notes

Reaction equation

HRID 1877066 reaction equation
[CH:1]1([CH:6]([C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]=2[CH3:19])O)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:22][CH:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:10][C:9]=1[CH3:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68509772Cyclopentyl(2-methyl-5-phenylfuran-3-yl)methanol

Product 1

HCID 685140893-[Chloro(cyclopentyl)methyl]-2-methyl-5-phenylfuranYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclopentyl(2-methyl-5-phenylfuran-3-yl)methanol (0.9 g) in toluene (20 mL) was added thionyl chloride (0.5 mL), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure to give the title compound (1.0 g, 100%) as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-33ed6ed5150244c3820f26b7b43f1c9b
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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