HCID 86714058, compound → HCID 86714060, compound

HRID 576350Notes

Reaction equation

HRID 576350 reaction equation
[CH2:1]([O:4][C:5]1[C:6](C=C)=[C:7]([CH:21]2[C@H:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:25]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:24]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C@@H:23]([CH2:51][O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[O:22]2)[CH:8]=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:10]=1[Cl:11])[CH:2]=[CH2:3]>C(Cl)Cl>[Cl:11][C:10]1[C:9]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)=[CH:8][C:7]([CH:21]2[C@H:26]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@@H:25]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C@H:24]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C@@H:23]([CH2:51][O:52][CH2:53][C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[O:22]2)=[C:6]2[C:5]=1[O:4][CH2:1][CH:2]=[CH:3]2

Participants

3

Reactant 1

HCID 86714058HCID 86714058, compound

Product 1

HCID 86714060HCID 86714060, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 83 (145 mg, 0.17 mmol) and Grubb's 2nd generation cat. (25 mg, 0.03 mmol) in CH2Cl2 (34 mL) was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 84 (120 mg, 82%) as colorless oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-58dd400be7b344969793fc52a98b8bc2
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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