1,4-Dioxaspiro[4.5]decan-8-one → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 1013052Notes

Reaction equation

HRID 1013052 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+]>CO>[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

4

Reactant 2

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

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-olYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a methanol (50 mL) solution of 1,4-dioxa-spiro[4.5]decan-8-one (5 g, 32 mmol) at 0° C. was added NaBH4 (1.34 g, 35.3 mmol) in 4 portions. The solution was stirred at 0° C. for 15 min followed by stirring at room temperature. for 1 hour. The methanol was evaporated and the residue partitioned between ether and water. The organic layer was separated, dried over Na2SO4 and concentrated to give the desired alcohol as a colorless oil (4.92 g). LC-MS (C8H14O3 calculated 158) m/z 159 (M+H); 1H NMR (300 MHz, CDCl3) δ 3.90 (s, 4H), 3.77 (m, 1H), 1.82 (m, 4H), 1.55 (m, 4 H).

Workup

  1. stirringby stirring at room temperature
  2. waitfor 1 hour
  3. customThe methanol was evaporated
  4. customthe residue partitioned between ether and water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7533cd2df9204428a4d3ec2e53f79d8e
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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