Borohydride → 3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

HRID 459912

Reaction equation

HRID 459912 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:7][O:6][C:5]2([CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[O:4][CH2:3]1.[BH4-]>CO>[CH3:1][C:2]1([CH3:14])[CH2:3][O:4][C:5]2([CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][CH2:12]2)[O:6][CH2:7]1

Participants

4

Reactant 2

HCID 28123BorohydrideHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-one

Product 1

HCID 124700963,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-one (Aldrich, 750 mg, 3.78 mmol) with polymer-supported borohydride (Aldrich, 3026 mg, 7.56 mmol) in methanol (30 mL). Shake by rotation the resulting mixture overnight. Filter the reaction mixture and concentrate the filtrate. Wash the residue with hydrochloric acid 0.1M and extract with EtOAc. Dry the organic layer over sodium sulfate, filter and concentrate.

Workup

  1. customthe resulting mixture overnight
  2. filtrationFilter the reaction mixture
  3. concentrationconcentrate the filtrate
  4. washWash the residue with hydrochloric acid 0.1M
  5. extractionextract with EtOAc
  6. dry with materialDry the organic layer over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-bfbde5ec2c73434e868e22d83e2af1ee
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Linked notes

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