Sodium borohydride → HCID 19390054, compound

HRID 1757229Notes

Reaction equation

HRID 1757229 reaction equation
[BH4-].[Na+].[OH:3][CH:4]1[CH2:16][CH2:15][C:7]2([CH2:12][CH2:11][CH:10]([CH:13]=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5]1>C(O)C>[OH:3][CH:4]1[CH2:5][CH2:6][C:7]2([CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 193900319-Hydroxyspiro[5.5]undecane-3-carboxaldehyde

Product 1

HCID 19390054HCID 19390054, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (65.0 mg) was added to a solution of 0.320 g 9-hydroxy-3-formyl-spiro[5.5]undecane in 5 ml of ethanol, at 0° C. under argon atmosphere. After 30 minutes the mixture was quenched with 2 ml. of 0.1N hydrochloric acid and evaporated under reduced pressure; the crude residue was dissolved in 10 ml. of ethyl acetate, the organic layer washed with water was dried over anhydrous sodium sulfate and evaporated to dryness to give 0.300 g of 9-hydroxy-3-hydroxymethyl-spiro[5.5]undecane as a transparent oil. TLC: Rf=0.35 (SiO2 plates, ethyl acetate/n-hexane 65/35). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 3.63 (1H, hept), 3.45 (2H, d), 2.05-0.95 (17H, m).

Workup

  1. customAfter 30 minutes the mixture was quenched with 2 ml
  2. customof 0.1N hydrochloric acid and evaporated under reduced pressure
  3. dissolutionthe crude residue was dissolved in 10 ml
  4. washof ethyl acetate, the organic layer washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0364c82319514ae2a009473a21b6c923
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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