Water → HCID 13071121, compound

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 dried 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).

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. dry with materialthe combined extracts are dried over sodium sulphate
7. distillationthe solvent is distilled off (at the conclusion under reduced pressure)

ORD record

ord-8ed1fe532b99410c800b75fb4823f461

Source dataset

uspto-grants-1976_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03950362