Sodium borohydride → HCID 178486948, compound

HRID 338519Notes

Reaction equation

HRID 338519 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][C:12](=[O:14])[CH2:11]2)=[C:6]([O:15][CH3:16])[CH:5]=1>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:11][C@H:12]([OH:14])[CH2:13]2)=[C:6]([O:15][CH3:16])[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86698847HCID 86698847, compound

Product 1

HCID 178486948HCID 178486948, compoundYield 77.18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.25 g, 6.75 mmol) was added to a solution of 3-(4-bromo-2-methoxyphenyl)cyclobutanone (1.87 g, 7.3 mmol) in tetrahydrofuran (70 mL) at 0° C., the reaction was stirred room temperature 1 hr, extracted with 1:1 solution of ethyl acetate in heptane, the organic layers was washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (1.34 g, 77.18%).

Workup

  1. extractionextracted with 1:1 solution of ethyl acetate in heptane
  2. washthe organic layers was washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eb680e306e0343bc867781db199cbaa2
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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