Phosgene → HCID 86746903, compound

HRID 1587144Notes

Reaction equation

[C:1](Cl)([Cl:3])=[O:2].[CH3:5][CH2:6][C@@H:7]([CH:32]([CH3:34])[CH3:33])/[CH:8]=[CH:9]/[C@H:10]([C@@H:12]1[C@@:16]2([CH3:31])[CH2:17][CH2:18][C@@H:19]3[C@@:24]4([CH3:30])[CH2:25][CH2:26][C@H:27]([OH:29])[CH2:28][C:23]4=[CH:22][CH2:21][C@H:20]3[C@@H:15]2[CH2:14][CH2:13]1)[CH3:11].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:3][C:1]([O:29][C@H:27]1[CH2:26][CH2:25][C@@:24]2([CH3:30])[C:23](=[CH:22][CH2:21][C@@H:20]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:31])[C@H:15]3[CH2:14][CH2:13][C@@H:12]2[C@H:10]([CH3:11])/[CH:9]=[CH:8]/[C@H:7]([CH:32]([CH3:33])[CH3:34])[CH2:6][CH3:5])[CH2:28]1)=[O:2]

Participants

Conditions

Temperature: -10 °C

Procedure

10 ml of a 20% phosgene solution in toluene are added to a solution, cooled to -10° C., of 4.12 g of stigmasterol in 40 ml of methylene chloride. The mixture is reacted overnight and then cooled to -10° C. After adding 0.7 ml of triethylamine in 10 ml of methylene chloride the reaction is continued for 24 hours. The mixture is neutralized with 0.7 ml of triethylamine in 10 ml of methylene chloride and the (E)-stigmasta-5,22-dien-3β-yl chloroformate is isolated.

Workup

customThe mixture is reacted overnight

Sources & evidence

ORD record: ord-02f69febecba475c8ad43468e061cc32
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215972

Reaction notes

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