Water → HCID 13071121, compound

HRID 267258Notes

Reaction equation

HRID 267258 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+].O>CO.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 3

HCID 962Water2×HCID 4311764Sodium borohydride2×HCID 15629417HCID 15629417, compound

Product 1

HCID 13071121HCID 13071121, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 340 mg (2mmols) of 2,5,11-trioxatricyclo[4,3,1,14,8 ]undecan-3-one in 10 ml of methanol are added all at once 150 mg of sodium borohydride while stirring and cooling to 12°-15°C(water bath). After 11/2 hours, during which time the bath temperature is allowed to rise to 20°C, a further 150 mg of sodium borohydride are added and the mixture is stirred for 21/2 hours at 20°C. The reaction mixture is then treated with 10 ml of water, the pH adjusted to 8 with a few drops of acetic acid, and concentrated under reduced pressure to about 3 ml. The concentrate is extracted three times with 25 ml of methylene chloride on each occasion, the combined extracts are dired over sodium sulphate and the solvent is distilled off (at the conclusion under reduced pressure) to give crystalline 3-hydroxymethyl-2,4-dioxabicyclo [3,3,1]nonan-7-ol of the formula IIa (m.p. 146°-149°C).

Workup

  1. custom2 hours
  2. customto rise to 20°C
  3. stirringthe mixture is stirred for 21/2 hours at 20°C
  4. concentrationconcentrated under reduced pressure to about 3 ml
  5. extractionThe concentrate is extracted three times with 25 ml of methylene chloride on each occasion
  6. distillationthe solvent is distilled off (at the conclusion under reduced pressure)

Sources & evidence

ORD record
ord-6fc72202e56244df90d804ade3720ec0
Source dataset
uspto-grants-1976_03
Patent number
US03941813

Reaction notes

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