Cholesterol → 3464-50-4

HRID 2231766Notes

Reaction equation

[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(N(CC)CC)C.[Cl:36][CH2:37][C:38](Cl)=[O:39]>C1C=CC=CC=1>[CH3:8][C@@H:7]([C@@H:9]1[C@@:27]2([CH3:28])[CH2:26][CH2:25][C@@H:24]3[C@@:22]4([CH3:23])[CH2:21][CH2:20][C@H:18]([O:19][C:38]([CH2:37][Cl:36])=[O:39])[CH2:17][C:16]4=[CH:15][CH2:14][C@H:13]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of cholesterol (1.93 g, 5 mmol) and triethylamine (0.51 g, 5 mmol) in benzene (25 mL) was added dropwise to an 8°-10° C. solution of chloroacetyl chloride (0.57 g, 5 mmol) in benzene (20 mL). The solution was heated under reflux at 80° C. for 24 hours, cooled to room temperature and worked up. Recrystallization (absolute EtOH) afforded the title compound (1.53 g, 66%) as a white solid (mp 160°-161° C.).

Workup

temperatureThe solution was heated
temperaturecooled to room temperature
customRecrystallization (absolute EtOH)

Sources & evidence

ORD record: ord-431fc5fe3e034b7baae6822ffb7135a1
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04783528

Reaction notes

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