Thionyl Chloride → 4-[chloro(2-methyl-5-phenylfuran-3-yl)methyl]tetrahydro-2H-pyran

HRID 1877037Notes

Reaction equation

HRID 1877037 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][C:6]=1[CH:7]([CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)O.S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][CH:7]([C:6]1[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:3][C:2]=1[CH3:1])[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68514112(2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol

Product 1

HCID 685124234-[chloro(2-methyl-5-phenylfuran-3-yl)methyl]tetrahydro-2H-pyranYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2-methyl-5-phenylfuran-3-yl) (tetrahydro-2H-pyran-4-yl)methanol (1.8 g) in toluene (20 mL) was added thionyl chloride (1.4 mL), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure to give the title compound (1.9 g, 100%) as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e72f28db2894c088dc58f41dc2592a1
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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