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

HRID 1631872Notes

Reaction equation

HRID 1631872 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 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Into a 250 ml round bottom flask is weighed 20 g of 1,4-dioxa-spiro[4.5]decan-8-one (128 mmol) and dissolved in 200 ml of methanol to give a pale yellow solution. The solution is cooled to 5° C. and sodium borohydride (4 g, 106 mmol) is added portionwise keeping the temperature below 20° C. Once the addition is complete the solution was stirred at room temperature for 3 hours. The reaction is evaporated to one third volume and then diluted with water, acidified carefully with 0.5 M aqueous hydrochloric acid, and extracted with diethyl ether (2×100 ml). The combined organics extracts are dried over magnesium sulphate, filtered and evaporated to give 1,4-dioxa-spiro[4.5]decan-8-ol (12.2 g).

Workup

  1. customInto a 250 ml round bottom flask is weighed
  2. customto give a pale yellow solution
  3. customthe temperature below 20° C
  4. additionOnce the addition
  5. customThe reaction is evaporated to one third volume
  6. additiondiluted with water
  7. extractionextracted with diethyl ether (2×100 ml)
  8. dry with materialThe combined organics extracts are dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-55fbaa2be7a1430d8e8ebf39ecea3dec
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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