Sulfuryl chloride → HCID 21876925, compound

HRID 723580Notes

Reaction equation

HRID 723580 reaction equation
[CH:1]1([O:6][C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:15])(=O)=O>ClCCl>[Cl:15][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[O:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 21876832HCID 21876832, compound

Product 1

HCID 21876925HCID 21876925, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-3-cyclopentyloxythiophene was prepared according to the procedures described in P. Stanetty and E. Puschautz, Monatshefte Chemie, 1989, 120, 65. Thus, to a solution of 3-cyclopentyloxythiophene (3.98 g, 23.7 mmol) in dichloromethane (35 mL) was added sulfuryl chloride (2 mL, 24.9 mmol) at 15° C. under argon. The mixture was stirred for 1 hour, then concentrated to dryness. Purification by flash chromatography (silica, 100% hexane) gave 2-chloro-3-cyclopentyloxythiophen (2.75 g, 59%) as a pale yellow oil; 1HNMR (300 MHz, CDCl3) δ 6.99 (d, J=6.0 Hz, 1H), 6.75 (d, J=6.0 Hz, 1H), 4.69–4.74 (m, 1H), 1.7–1.93 (m, 6H), 1.5–1.7 (m, 2H). MS m/e (%): 202 (M+; 6).

Workup

  1. custom2-Chloro-3-cyclopentyloxythiophene was prepared
  2. concentrationconcentrated to dryness
  3. customPurification by flash chromatography (silica, 100% hexane)

Sources & evidence

ORD record
ord-d80bac5a7ef345da931501a3174366c9
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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