Methanol → HCID 66961660, compound

HRID 1446565Notes

Reaction equation

HRID 1446565 reaction equation
[BH4-].[Na+].[Br:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[C:5]1=[O:14].CO.O>O1CCCC1.C(OCC)(=O)C>[Br:3][C@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[C@H:5]1[OH:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 110316412-Bromo-5-fluoro-1-indanone

Product 1

HCID 66961660HCID 66961660, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (2.09 g) was added to a solution of 2-bromo-5-fluoroindan-1-one (8.43 g) in a mixture of tetrahydrofuran (120 mL) with methanol (30 mL) while cooling with ice, and the reaction solution was stirred for 20 minutes. Water and ethyl acetate were added to the reaction solution while cooling with ice and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting solid was washed with heptane to obtain 7.54 g of the title compound. The physical properties of the compound are as follows.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. customthe organic layer was partitioned
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe resulting solid was washed with heptane

Sources & evidence

ORD record
ord-601869a2ea3b4fbb8a2872d5d3407539
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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