Chloral Hydrate → HCID 68143795, compound

HRID 1415065Notes

Reaction equation

HRID 1415065 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].[Cl:22][C:23]([Cl:28])([Cl:27])[CH:24](O)[OH:25]>C1C=CC=CC=1>[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[O:21][CH:24]([OH:25])[C:23]([Cl:28])([Cl:27])[Cl:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

4

Reactant 2

HCID 2707Chloral HydrateHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 68143795HCID 68143795, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Add 2.9 g. of dl-13-ethyl-17β-hydroxygon-4-en-3-one to a solution of 1.9 g. of chloral hydrate in 10 ml. of benzene at 5°C. Keep the mixture overnight at this temperature. Filter off the product and recrystallize it successively from ethyl acetate and petroleum ether-benzene to obtain the title substance, m.p. 175°-176°; ultraviolet peak at 240 mμ (ε17,500); infrared peaks at 3.10, 6.05, 6.20 μ.

Workup

  1. additionAdd 2.9 g
  2. customat 5°C
  3. customthe mixture overnight
  4. filtrationFilter off the product
  5. customrecrystallize it successively from ethyl acetate and petroleum ether-benzene
  6. customto obtain the title substance, m.p. 175°-176°

Sources & evidence

ORD record
ord-a1baf57b7bb14360968cd7c3042b4ab9
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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