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

HRID 1349379Notes

Reaction equation

HRID 1349379 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+].P([O-])([O-])([O-])=O.C(OCC)C>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

6

Reactant 4

HCID 1061PhosphateHCID 3283Diethyl EtherHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-olYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

350 g of 1,4-dioxa-spiro[4.5]decan-8-one were suspended in 2000 ml of ethanol, and 28.1 g of sodium borohydride were added in portions while cooling with an ice bath. After stirring overnight at room temperature, first 750 ml of phosphate buffer (pH 7, Merck-Darmstadt) and then 1000 ml of diethyl ether were added, with stirring, and precipitated solids were filtered and then washed with diethyl ether. The filtrate was dried over sodium sulfate, filtered and concentrated. 345 g of 1,4-dioxa-spiro[4.5]decan-8-ol were obtained in the form of a white solid.

Workup

  1. temperaturewhile cooling with an ice bath
  2. stirringwith stirring
  3. customprecipitated solids
  4. filtrationwere filtered
  5. washwashed with diethyl ether
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-07f472c854a24a0dafcd9d8e104f1984
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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