Sodium borohydride → HCID 59199367, compound

HRID 2089548Notes

Reaction equation

HRID 2089548 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:14])[C:5]([CH3:13])([CH3:12])[C:6]2=[O:11].[BH4-].[Na+]>C(O)C.[NH4+].[Cl-]>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:14])[C:5]([CH3:12])([CH3:13])[CH:6]2[OH:11]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59199412HCID 59199412, compound

Product 1

HCID 59199367HCID 59199367, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of chloro-2,2-dimethyl-indan-1,3-dione (1.82 g, 8.7 mmol) in ethanol (100 mL) at −40° C. is added NaBH4 (100 mg, 2.6 mmol). The reaction is warmed to −20° C. and stirred for 1 hour. The reaction is diluted with saturated aqueous NH4Cl and concentrated in vacuo to remove the volatile organics. The mixture is then diluted with ethyl acetate and the layers are separated. The aqueous layer is extracted an additional time with ethyl acetate and the organic layers are combined, dried over Na2SO4, filtered and concentrated to afford 7-chloro-3-hydroxy-2,2-dimethyl-indan-1-one without the need for further purification; MS: (ESI) m/z 211.15 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the volatile organics
  3. additionThe mixture is then diluted with ethyl acetate
  4. customthe layers are separated
  5. extractionThe aqueous layer is extracted an additional time with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0e4d47327b6541669975db9349f8c0ba
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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