Benzo(b)thiophene-3(2H)-one 1,1-dioxide → HCID 12067740, compound

HRID 734367Notes

Reaction equation

HRID 734367 reaction equation
CO[CH:3]=[CH:4][CH:5]([O:8][CH3:9])OC.[S:10]1(=[O:21])(=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[CH2:11]1>>[CH3:9][O:8]/[CH:5]=[CH:4]/[CH:3]=[C:11]1/[S:10](=[O:20])(=[O:21])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]/1=[O:19]

Participants

3

Reactant 2

HCID 70780Benzo(b)thiophene-3(2H)-one 1,1-dioxideHCID 865871-Propene, 1,3,3-trimethoxy-

Product 1

HCID 12067740HCID 12067740, compoundYield 75.1%

Conditions

Temperature
90 °C

Procedure

A mixture of 1,3,3-trimethoxypropene (2.64 g, 20 mmol) and 1.82 g (10 mmol) of 1-benzothiophen-3(2H)-one 1,1-dioxide was heated at 90° C. for 12 h. The solid formed was recrystallized from MeOH to give 1.88 g (75% yield) of final product. 1H NMR (400 MHz, CDCl3): δ 4.02 (s, 3H, OCH3), 6.51 (t, 3JH—H=12.3 Hz, 1H), 7.51-8.11 (m, 6H). GC-MS (70 eV) m/e (relative intensity): 250 (65, M+), 219 (100, (M−OCH3)+).

Workup

  1. customThe solid formed
  2. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-22d156e08f2242c09fd6855a4f384529
Source dataset
uspto-grants-2009_09
Patent number
US07592188B2

Reaction notes

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