Acetic Anhydride → HCID 22790410, compound

HRID 1414968Notes

Reaction equation

HRID 1414968 reaction equation
[CH3:1][C@:2]12[CH2:10][CH2:9][C:8]3[C:11]4[CH:12]=[CH:13][C:14]([OH:19])=[CH:15][C:16]=4[CH2:17][CH2:18][C:7]=3[C:6]1=[CH:5][CH2:4][C:3]2=[O:20].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[CH3:1][C@:2]12[CH2:10][CH2:9][C:8]3[C:11]4[CH:12]=[CH:13][C:14]([O:19][C:21](=[O:23])[CH3:22])=[CH:15][C:16]=4[CH2:17][CH2:18][C:7]=3[C:6]1=[CH:5][CH2:4][C:3]2=[O:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2723425813beta-Methyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17one

Product 1

HCID 22790410HCID 22790410, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Mix 13β-methyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17-one with pyridine (3 cc) and acetic anhydride (1 cc) and keep at room temperature for 4 hours. Add ethanol (1 cc) and remove low-boiling material under reduced pressure (0.1 mm) to leave a red gum which crystallizes from a mixture of ethyl acetate and light petroleum. Recrystallize from methanol to obtain crystals of 13β-methyl-3-acetoxygona-1,3,5(10),8,14-pentaen-17-one, melting partially at 161°-166° with resolidification at about 220° and finally melting at 260°-265° (decomp.); infrared absorption peaks at 5.75 μ and 8.27 μ, with absence of an absorption band due to a hydroxy group; ultraviolet absorption peak at 307.5 mμ (ε24,000).

Workup

  1. customAdd ethanol (1 cc) and remove low-boiling material under reduced pressure (0.1 mm)
  2. customto leave a red gum which
  3. customcrystallizes from a mixture of ethyl acetate and light petroleum
  4. customRecrystallize from methanol

Sources & evidence

ORD record
ord-5e2deac5b820485ca52c7503fb0aef28
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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