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

HRID 1088726Notes

Reaction equation

HRID 1088726 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

HCID 14820507HCID 14820507, compound

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-21f4d63ecb4b4ef0ab3057156aeacea2
Source dataset
uspto-grants-1990_10
Patent number
US04963580

Reaction notes

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