Acetyl chloride → HCID 68143211, compound

HRID 1077233Notes

Reaction equation

HRID 1077233 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].[C:22](OC(=O)C)(=[O:24])[CH3:23].[C:29](Cl)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:22]([O:20][C:15]1[CH2:14][CH2:13][C@H:12]2[C:17](=[CH:18][CH2:19][C@H:8]3[C@H:7]4[C@@:3]([CH2:1][CH3:2])([CH:4]([O:21][C:29](=[O:31])[CH3:30])[CH2:5][CH2:6]4)[CH2:11][CH2:10][C@@H:9]32)[CH:16]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 68143211HCID 68143211, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reflux dl-13-ethyl-17β-hydroxygon-4-en-3-one (3.0 g) with acetic anhydride (45 cc), acetyl chloride (24 cc) and pyridine (2.4 cc) for three hours. Take to dryness under reduced pressure and partition the residue between benzene-ether and water. Triturate the crude product with hot ether to obtain dl-3,17-diacetoxy-13-ethylgona-3,5-diene (3.125 g), m.p. 148°-156°; λ max. KBr 5.68, 5.78, 6.0, 6.11 μ; λ max. EtOh 238 mμ (ε19,500).

Workup

  1. custompartition the residue between benzene-ether and water
  2. customTriturate the crude product with hot ether

Sources & evidence

ORD record
ord-d010c40014244278b7d3d8f0f119c74c
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

Loading…