Oxalyl chloride → 4,5,6,7-Tetrahydro-benzo[b]thiophene-2-carbonyl chloride

HRID 551861

반응식

HRID 551861 반응식
[S:1]1[C:5]([C:6](O)=[O:7])=[CH:4][C:3]2[CH2:9][CH2:10][CH2:11][CH2:12][C:2]1=2.C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[S:1]1[C:5]([C:6]([Cl:16])=[O:7])=[CH:4][C:3]2[CH2:9][CH2:10][CH2:11][CH2:12][C:2]1=2

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 20634434,5,6,7-Tetrahydro-1-benzothiophene-2-carboxylic acid

생성물 1

HCID 64853624,5,6,7-Tetrahydro-benzo[b]thiophene-2-carbonyl chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

4,5,6,7-Tetrahydro-benzo[b]thiophene-2-carboxylic acid (1.0 g, 5.50 mmol) is dissolved in dichloromethane [DCM] (25 mL) that contains 5 drops of N,N-dimethylformamide [DMF] under nitrogen and cooled to 0° C. Oxalyl chloride (13.7 mL of a 2.0M solution in DCM) is added via syringe and allowed to warm to RT over 1 hour. All solvent is then removed under reduced pressure, and the resultant oil is reduced from toluene (3×20 mL) to remove residual oxalyl chloride. The residue is then dissolved in ethyl acetate and washed with saturated sodium bicarbonate (1×100 mL), then washed with saturated sodium chloride (1×100 mL) and dried over sodium sulfate. The solution is then filtered and concentrated under reduced pressure to give 4,5,6,7-tetrahydro-benzo[b]thiophene-2-carbonyl chloride (1) as an off-white solid (1.03 g).

후처리

  1. temperatureto warm to RT over 1 hour
  2. customAll solvent is then removed under reduced pressure
  3. customto remove residual oxalyl chloride
  4. dissolutionThe residue is then dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate (1×100 mL)
  6. washwashed with saturated sodium chloride (1×100 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution is then filtered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0f89938f0f464b328e205671582d1545
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947835B2

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