Sodium borohydride → HCID 13071121, compound

HRID 1605389Notes

Reaction equation

HRID 1605389 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([O:10][CH:4]([O:5]3)[C:3](=[O:12])[O:2]1)[CH2:9]2.[BH4-].[Na+]>C(O)C.O.C(O)(=O)C>[OH:12][CH2:3][CH:4]1[O:10][CH:8]2[CH2:7][CH:6]([CH2:11][CH:1]([OH:2])[CH2:9]2)[O:5]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 15629417HCID 15629417, compound

Product 1

HCID 13071121HCID 13071121, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 340 mg of 2,5,11-trioxatricyclo[4,3,1,14,8 ]undecan-3-one of the formula Ia in 10 ml of absolute ethanol is treated at room temperature with 150 mg of sodium borohydride and the mixture is stirred for 2 hours. The reaction mixture is diluted with 10 ml of water, the pH adjusted to 8 with a few drops of glacial acetic acid and the resulting solution is concentrated under reduced pressure to about 3 ml. The concentrate is extracted three times with altogether 100 ml of methylene chloride, the combined extracts are dried with sodium sulphate and the solvent is distilled off to give 3-hydroxymethyl-2,4-dioxabicyclo[3,3,1]nonan-7-ol of the formula IIa, which melts at 146°-149°C.

Workup

  1. concentrationthe resulting solution is concentrated under reduced pressure to about 3 ml
  2. extractionThe concentrate is extracted three times with altogether 100 ml of methylene chloride
  3. dry with materialthe combined extracts are dried with sodium sulphate
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-6ea4c3d57ac247aebf2df845377b602b
Source dataset
uspto-grants-1976_04
Patent number
US03950362

Reaction notes

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