Benzene → HCID 69411949, compound

HRID 2187264Notes

Reaction equation

HRID 2187264 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([C:16]([CH3:36])([CH3:35])[C@@H:17]([O:27][Si](C(C)(C)C)(C)C)[CH2:18][CH2:19]2)=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7].[CH:38]1C=CC=CC=1.Cl>C(O)C>[CH2:1]([O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C:11]([C:12]3[CH2:13][CH2:14][C@@H:15]4[C@:20]([C:22]=3[CH2:23][CH2:24]2)([CH3:21])[CH2:19][CH2:18][C@H:17]([OH:27])[C:16]4([CH3:35])[CH3:36])=[CH:10][CH2:9]1)[CH3:7])[CH3:38]

Participants

5

Reactant 3

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 69411642HCID 69411642, compound

Product 1

HCID 69411949HCID 69411949, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethylchola-5,7-dien-24-oic acid methyl ester (4.0 g) is suspended in a mixture of 60 ml of 96% ethanol, 10.1 ml of benzene and 10.1 ml of concentrated hydrogen chloride acid and refluxed for 3.5 hours. After aqueous work-up and column chromatography followed by crystallization from ethanol the title compound (1.37 g) is isolated. Melting point: 122-124° C. 1H-NMR (CDCl3, 300 MHz): δ=5.35 (1H, s); 4.13 (2H, q); 3.25 (1H, m). 1.25 (3H, t). MS: Calculated: 428.7. Found 428.3.

Workup

  1. temperaturerefluxed for 3.5 hours
  2. customAfter aqueous work-up and column chromatography followed by crystallization from ethanol the title compound (1.37 g)
  3. customis isolated

Sources & evidence

ORD record
ord-1992ecc40f0a4379b565a088f355cb2f
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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