Water → HCID 57750763, compound

HRID 900996Notes

Reaction equation

HRID 900996 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10]OC)[CH:9]=1.B(Cl)(Cl)[Cl:15].O>ClCCl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][Cl:15])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 57750764HCID 57750764, compound

Product 1

HCID 57750763HCID 57750763, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (4-methoxymethyl-thiophen-2-yl)-acetic acid methyl ester (0.70 g, 3.50 mmol) in dichloromethane (20 mL) is treated with boron trichloride (3.50 mL, 1.0 M, 3.50 mmol) in a dropwise maner. After stirring at room temperature for 30 min the mixture is poured into water and extracted with dichloromethane (3×). The combined organic layers are washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue is purified by chromatography (silica gel, 5-10% ethyl acetate in heptane) to give (4-chloromethyl-thiophen-2-yl)-acetic acid methyl ester (0.58 g, 81%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 7.18 (s, 1 H), 6.95 (s, 1 H), 4.52 (s, 2 H), 3.80 (s, 2 H), 3.72 (s, 3 H).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washThe combined organic layers are washed with saturated aq NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified by chromatography (silica gel, 5-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f23a41db597d4b869f5591d206efbe96
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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