Methanol → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 1752449Notes

Reaction equation

HRID 1752449 reaction equation
[BH4-].[Na+].CO.[O:5]1[C:9]2([CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[O:8][CH2:7][CH2:6]1>O>[O:5]1[C:9]2([CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaBH4 (370 mg, 10 mmol) in 5 mL H2O was slowly added to 10 mL of MeOH solution of 1,4-dioxaspiro[4.5]decan-8-one (1.56 g, 10 mmol) at 0° C. After the addition, the methanol was removed and the residue was extracted with EtOAc (2×20 mL). The EtOAc layer was dried over MgSO4, filtered, and evaporated to give 1,4-dioxaspiro[4.5]decan-8-ol (compound 35-1), which was used in next step without further purification (1.56 g, yield 100%).

Workup

  1. additionAfter the addition
  2. customthe methanol was removed
  3. extractionthe residue was extracted with EtOAc (2×20 mL)
  4. dry with materialThe EtOAc layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ed8ba5c33d0c4823ae2956102ca186d1
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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