Water → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 322067Notes

Reaction equation

HRID 322067 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+].O>C(O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-olYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A stirred, cooled (5° C.) solution of 1,4-dioxaspiro[4.5]decan-8-one (20 g, 0.128 mol) in ethanol (250 ml) was treated with sodium borohydride (7.3 g, 0.192 mol) in portions over 20 minutes. The reaction mixture was stirred at 5° C. for 1 hour then at room temperature for 1 hour. Water (20 ml) was added and the mixture was stirred vigorously for 10 minutes then concentrated in vacuo. The residue was partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated and the aqueous re-extracted with ethyl acetate (100 ml). The combined organics were dried (sodium sulphate) then evaporated to give the title alcohol as a colourless oil (17.1 g, 84%). MS ES+, m/z=159 for (M+H)+; δ(360 MHz, CDCl3) 1.52-1.71 (4H, m), 1.78-1.92 (4H, m), 3.76-3.83 (1H, m), 3.91-3.94 (4H, m).

Workup

  1. waitat room temperature for 1 hour
  2. stirringthe mixture was stirred vigorously for 10 minutes
  3. concentrationthen concentrated in vacuo
  4. customThe residue was partitioned between water (100 ml) and ethyl acetate (100 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous re-extracted with ethyl acetate (100 ml)
  7. dry with materialThe combined organics were dried (sodium sulphate)
  8. customthen evaporated

Sources & evidence

ORD record
ord-c74d9eb17e664fc29ff750d6c946ea7b
Source dataset
uspto-grants-2001_04
Patent number
US06211219B1

Reaction notes

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