HCID 72270955, compound → HCID 72270946, compound

HRID 712793Notes

Reaction equation

HRID 712793 reaction equation
[CH2:1]([N:4]([CH:15]([CH2:35][CH:36]=C)[CH2:16][O:17][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[Si:18]([O:17][CH2:16][CH:15]1[CH2:35][CH:36]=[CH:2][CH2:1][N:4]1[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:6])=[O:7])([C:31]([CH3:32])([CH3:34])[CH3:33])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 72270955HCID 72270955, compound

Product 1

HCID 72270946HCID 72270946, compoundYield 132%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-allyl-N-(1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl)-4-methylbenzenesulfonamide (D10) (7.12 g, 13.33 mmol) in DCM (64 ml), Grubb's catalyst (1.09 g, 1.32 mmol) was added and the mixture was stirred at RT overnight. After solvent evaporation, the residue was loaded on KP-Si (100 g) cartridge eluting with a mixture cHex/EtOAc from 100/0 to 90/10. Collected fractions after solvent evaporation afforded the title compound (D11) (8.9 g).

Workup

  1. customAfter solvent evaporation
  2. washeluting with a mixture cHex/EtOAc from 100/0 to 90/10
  3. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-61be521c72594d4daf7dd0aab939fdec
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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