Borohydride → HCID 18476198, compound

HRID 2187639Notes

Reaction equation

HRID 2187639 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]([CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][C:4]=2[CH:3]=1.[BH4-]>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 28123BorohydrideHCID 54000908HCID 54000908, compound

Product 1

HCID 18476198HCID 18476198, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.36 g (1.36 mmol) of 5-chloro-2-(hepten-1-yl)benzo[b]thiophene in 50 ml methanol were added 5 g (15 mmol) of borohydride exchange resin and 375 mg (1.51 mmol) Ni(II)acetate tetrahydrate, and the mixture was refluxed for 1 h. It was cooled to room temperature and the resin removed by filtration. The resin was heated twice with 50 ml methanol, and the combined filtrates were concentrated under reduced pressure. The residue was eluted through a column of silica gel with hexane, and the eluant was evaporated to give 175 mg (48%) of the title compound as a colorless resinous oil; MS 266 (M+).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. customthe resin removed by filtration
  3. temperatureThe resin was heated twice with 50 ml methanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. washThe residue was eluted through a column of silica gel with hexane
  6. customthe eluant was evaporated

Sources & evidence

ORD record
ord-59ec33cfe79e4d87b97322d584825494
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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