Isopropanol → HCID 67119272, compound

HRID 2076674Notes

Reaction equation

HRID 2076674 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[C:22]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][C:41]([CH2:44][C:45]([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)[C:18]=1[C:19]([OH:21])=[O:20])[CH:14]=[CH2:15].[CH3:51][CH:52](O)[CH3:53].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([O:16][C:17]1[C:25]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:23]=[C:22]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:39]=[CH:40][C:41]([CH2:44][C:45]([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])=[CH:42][CH:43]=3)=[CH:34][CH:33]=2)[C:18]=1[C:19]([O:21][CH:52]([CH3:53])[CH3:51])=[O:20])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67119339HCID 67119339, compound

Product 1

HCID 67119272HCID 67119272, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (108 μl, 0.68 mmol) was added to a solution of 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid (150 mg, 0.29 mmol), 2-propanol (26 μl, 0.34 mmol) and triphenylphosphine (180 mg, 0.68 mmol) in tetrahydrofuran (3 ml) at room temperature. After the mixture was stirred at room temperature for 1 hour, the solvent of the reaction mixture was removed under reduced pressure. The obtained residue was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=4/1) to give isopropyl 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (141 mg, yield: 87%).

Workup

  1. customthe solvent of the reaction mixture was removed under reduced pressure
  2. customThe obtained residue was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-552097c42200401987ddddb74a2292fd
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

Loading…