Ethanol → (3-Ethoxypyridin-2-yl)methanol

3-Hydroxy-2-hydroxymethylpyridine (8.5 g) was added to a solution of sodium (1.565 g) in ethanol (100 cc) and the mixture was evaporated to dryness. Dimethylsulphoxide (180 cc) was added to the residue, and bromoethane (7.43 g) in dimethylsulphoxide (24 cc) was added over 20 minutes to the stirred mixture. The mixture was allowed to stand at room temperature for 65 hours, and was evaporated. The residue was partitioned between chloroform and water, and the chloroform extracts were evaporated to an oil which was converted into a crystalline hydrochloride m.p. 190°-191.5° by the addition of ethanolic hydrogen chloride. The hydrochloride was dissolved in water, and aqueous ammonia was added until the mixture was basic, and the mixture was extracted with chloroform. The chloroform extracts were evaporated and the residue crystallised from ethanol/diethyl ether to give 3-ethoxy-2-hydroxymethylpyridine (5.0 g) m.p. 74.5°-76°.

1. customthe mixture was evaporated to dryness
2. additionDimethylsulphoxide (180 cc) was added to the residue, and bromoethane (7.43 g) in dimethylsulphoxide (24 cc)
3. additionwas added over 20 minutes to the stirred mixture
4. customwas evaporated
5. customThe residue was partitioned between chloroform and water
6. customthe chloroform extracts were evaporated to an oil which
7. additionwas converted into a crystalline hydrochloride m.p. 190°-191.5° by the addition of ethanolic hydrogen chloride
8. dissolutionThe hydrochloride was dissolved in water
9. additionaqueous ammonia was added until the mixture
10. extractionthe mixture was extracted with chloroform
11. customThe chloroform extracts were evaporated
12. customthe residue crystallised from ethanol/diethyl ether

ORD record

ord-d7a9e2bb9b25472d936dde17152d90b0

Source dataset

uspto-grants-1978_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04083983