Azobisisobutyronitrile → HCID 67074567, compound

HRID 1944092Notes

Reaction equation

[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH2:50]I)[CH2:48]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1.CO>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH3:48])[CH3:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-bis-iodomethyl-tetrahydro-pyran (100 mg, 0.10 mmole) in toluene (2 mL), tristrimethylsilllylsilane (0.1 mL), AIBN (12 mg) was added and heated at 120° C. for 24 hour in a sealed tube. The reaction mixture was diluted with methanol and evaporated, washed with water (10 mL) and extracted with Ethyl acetate (3×15 mL). The crude product obtained after the removal of solvent to furnish 100 mg of crude (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran.

Workup

customevaporated
washwashed with water (10 mL)
extractionextracted with Ethyl acetate (3×15 mL)
customThe crude product obtained
customafter the removal of solvent

Sources & evidence

ORD record: ord-d6d4d88b72a24ee49cd033623e42a935
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394772B2

Reaction notes

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