Borane;tetrahydrofuran → HCID 19815618, compound

HRID 466192Notes

Reaction equation

HRID 466192 reaction equation
B.C1COCC1.[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[S:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][C:13]=2[CH:21]=1>C1COCC1>[OH:19][CH2:18][CH:15]1[CH2:14][C:13]2[CH:21]=[C:9]([O:8][CH3:7])[CH:10]=[CH:11][C:12]=2[S:17][CH2:16]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 19815616HCID 19815616, compound

Product 1

HCID 19815618HCID 19815618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The starting material is prepared as follows: Borane-THF complex (1M in THF, 55.4 ml, 55.4 mmol) is cooled to 0° C. To this mixture is added 6-methoxy-3,4-dihydro-2H-1-benzothiopyran-3-carboxylic acid (6.1 g, 25 mmol) in 30 ml of THF dropwise. The cooling bath is then removed and the mixture is stirred overnight. This is quenched by addition of 50% aqueous acetic acid (8 ml), and concentrated in vacuo at 50° C. The residue is purified by flash chromatography (silica gel, 40% EtOAc/hexane) to give 3-hydroxymethyl-6-methoxy-3,4-dihydro-2H-1-benzothiopyran as an oil which crystallizes on standing.

Workup

  1. customThe starting material is prepared
  2. customThe cooling bath is then removed
  3. customThis is quenched by addition of 50% aqueous acetic acid (8 ml)
  4. concentrationconcentrated in vacuo at 50° C
  5. customThe residue is purified by flash chromatography (silica gel, 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-0a2d665b3ade443583ca5335057b4a90
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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