Ammonia → 3-[(Hept-1-en-1-yl)sulfanyl]propane-1,2-diol

Lithium (1.61 g., 0.234 eq.) cut into small pieces is added to 150 ml. of dry liquid ammonia with stirring. After 5 minutes, 100 ml. of dry ether is added followed by the dropwise addition of 1-ethylthio-1-heptene (18.6 g., 0.117 moles). At the end of the addition, the blue color of the solution disappears and the reaction mixture is a white milky suspension. Ammonium chloride (6.26 g., 0.117 moles) is added cautiously followed by 1-bromo-2,3-propanediol (19.9 g., 0.128 moles). After stirring for 30 minutes, the ammonia is allowed to evaporate and water and ether are added to the residue. The aqueous layer is extracted once with ether and the ether extracts are combined and dried over MgSO4. The residue obtained after concentration of the ether is distilled (bp 129°-133° C, 0.15 mm.) to afford 6 g. of a yellow liquid. The liquid is further purified by column chromatography on SilicAR, CC-7, eluting with acetone:chloroform (1:5) to afford 3-(1-heptenylthio)-1,2-propanediol as a colorless liquid (5.7 g., 23.9%); nD24.1 1.5091.

1. additionis added to 150 ml
2. additionAt the end of the addition
3. customto evaporate
4. additionwater and ether are added to the residue
5. extractionThe aqueous layer is extracted once with ether
6. dry with materialdried over MgSO4
7. customThe residue obtained after concentration of the ether
8. distillationis distilled (bp 129°-133° C, 0.15 mm.)
9. customto afford 6 g
10. customThe liquid is further purified by column chromatography on SilicAR, CC-7
11. washeluting with acetone:chloroform (1:5)

ORD record

ord-3eb12139c47a403a95533de94ed96962

Source dataset

uspto-grants-1978_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04086278