Acetyl chloride → HCID 68143211, compound

HRID 1415053Notes

Reaction equation

HRID 1415053 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 3 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°; λmax. KBr 5.68, 5.78, 6.0, 6.11 μ; λmax. 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-0b4e0a53f89c44b8a40686c27290be36
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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