Water → HCID 23321618, compound

HRID 280080Notes

Reaction equation

HRID 280080 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[CH2:4][CH2:3][O:2]1.[BH4-].[Na+].O>C(O)C>[CH2:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[CH2:4][CH2:3][O:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 233216152-Oxaspiro[4.5]decan-8-one

Product 1

HCID 23321618HCID 23321618, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-oxaspiro[4.5]decan-8-one (46.4 g., 0.3 mole) from Part C above in 1.5 liters of absolute ethanol was stirred under N2 atmosphere while sodium borohydride was added in 1-1.5-g. portions. When the addition was completed the mixture was stirred at room temperature for 4 hours. Then 1445 ml. of water was added and stirring was continued for 30 minutes. Ethanol was removed in vacuo and the aqueous layer was extracted with chloroform to give 43 g. (91%) of a mixture of two isomers by TLC analysis and NMR spectral analysis. H-NMR δ (ppm) 1.02-1.79 (10H, multiplet); 3.24-3.95 (5H, multiplet); mass spectrum m/e 156 (M+).

Workup

  1. additionwas added in 1-1.5-g
  2. additionWhen the addition
  3. stirringstirring
  4. waitwas continued for 30 minutes
  5. customEthanol was removed in vacuo
  6. extractionthe aqueous layer was extracted with chloroform
  7. customto give 43 g

Sources & evidence

ORD record
ord-e51c48cd49314e009222070e694005a1
Source dataset
uspto-grants-1986_05
Patent number
US04588591

Reaction notes

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