Benzo[b]thiophene-5-ol, 2,3-dihydro- → HCID 14820507, 화합물

HRID 1088726노트

반응식

HRID 1088726 반응식
C(C1C2CCSC=2C=CC=1)C=C.[CH2:13]([C:16]1[CH:24]=[CH:23][C:19]2[CH2:20][CH2:21][S:22][C:18]=2[CH:17]=1)[CH:14]=[CH2:15].[OH:25]C1C=CC2SCCC=2C=1>>[CH2:13]([C:16]1[C:24]([OH:25])=[CH:23][C:19]2[CH2:20][CH2:21][S:22][C:18]=2[CH:17]=1)[CH:14]=[CH2:15]

참가 물질

4

반응물 3

HCID 11367101Benzo[b]thiophene-5-ol, 2,3-dihydro-HCID 22161964HCID 22161964, 화합물HCID 22161965HCID 22161965, 화합물

생성물 1

HCID 14820507HCID 14820507, 화합물

실험 절차

To a solution of BCl3 in methylene chloride (5.5 mL, 1.0M, 5.5 mmole) under N2 at -25° C. was added dropwise a solution of 5-allyloxy-2,3-dihydrobenzothiophene (1.0 g, 5.2 mmole) in methylene chloride (10 mL) keeping the temperature between -25° and -15° C. (10 minutes). The reaction mixture was stirred at -15° C. for 15 minutes. The cooling bath was then removed and the reaction mixture allowed to stir for another 1.5 hours. The reaction mixture was then poured into ice water (70 mL). An additional portion of methylene chloride (10 mL) was added and the layers separated. The aqueous layer was extracted an additional 2×20 mL methylene chloride and the combined organic layers were washed with NaHCO3 (sodium bicarbonate) (1×20 mL), H2O (1×20 mL) and brine (1×20 mL). After drying over Na2SO4, filtration and concentration afforded 0.56 g crude product. Purification by flash chromatography (90/10 hexane/EtOAc to elute) afforded, in order of elution: 64 mg (6.4%) 4-allyl-2,3-dihydrobenzothiophene (oil) 204 mg (20.4% 6-allyl-2,3-dihydrobenzothiophene (oil) and 146 mg (18.4%) 5-hydroxy-2,3-dihydrobenzothiophene.

후처리

  1. customPurification
  2. washby flash chromatography (90/10 hexane/EtOAc to elute)
  3. customafforded, in order of elution

출처 및 근거

ORD 기록
ord-21f4d63ecb4b4ef0ab3057156aeacea2
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963580

반응 노트

불러오는 중…