Boron trifluoride etherate → HCID 69411695, compound

HRID 2187266Notes

Reaction equation

HRID 2187266 reaction equation
[OH:1][C@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:4]([CH2:5][CH2:6][C:7]3[C:8]4[C@:19]([CH3:27])([CH2:20][CH2:21][C:22]=32)[C@@H:11]([C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH:9]=4)[C:3]1([CH3:29])[CH3:28].B(F)(F)F.CCO[CH2:37][CH3:38]>C1(O)CCCCC1>[CH:38]1([O:16][C:15](=[O:17])[CH2:14][CH2:13][C@H:12]([C@@H:11]2[C@:19]3([CH3:27])[C:8]([C:7]4[CH2:6][CH2:5][C@@H:4]5[C@:23]([C:22]=4[CH2:21][CH2:20]3)([CH3:26])[CH2:24][CH2:25][C@H:2]([OH:1])[C:3]5([CH3:28])[CH3:29])=[CH:9][CH2:10]2)[CH3:18])[CH2:37][CH2:4][CH2:3][CH2:2][CH2:25]1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 69410833HCID 69410833, compound

Product 1

HCID 69411695HCID 69411695, compound

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Conditions

Temperature
57.5 °C

Procedure

3β-Hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid (0.2 g) is suspended in 10 ml of cyclohexanol, 0.1 ml of boron trifluoride diethyl etherate is added and the mixture is stirred at 55-60° C. for 20 hours. After evaporation to dryness under reduced pressure, the remanens is purified by column chromatography and crystallized from methanol to give the title compound (49 mg). Melting point: 130-132° C. 1H-NMR (CDCl3): δ=5.35 (1H, s); 4.75 (1H, m); 3.24 (1H, m). MS: Calculated: 482.8. Found 482.4.

Workup

  1. customAfter evaporation to dryness under reduced pressure
  2. customthe remanens is purified by column chromatography
  3. customcrystallized from methanol

Sources & evidence

ORD record
ord-aeb7025f25f147b29a205e29ebda7f2e
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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