Diisopropylethylamine → Allyl (1-{4-[methoxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate

HRID 2240638Notes

Reaction equation

HRID 2240638 reaction equation
[CH2:1]([O:4][C:5](=[O:28])[NH:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:27])=[C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][C:18]3=[O:26])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)[CH:2]=[CH2:3].F[B-](F)(F)F.[CH3:34][O+](C)C.C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([O:4][C:5](=[O:28])[NH:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:27][CH3:34])=[C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][C:18]3=[O:26])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)2×HCID 178459818HCID 178459818, compound

Product 1

HCID 72252277Allyl (1-{4-[methoxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of allyl(1-{4-[hydroxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate, 0.78 g of trimethyloxonium tetrafluoroborate (Meerwein salt), and 1 mL of diisopropylethylamine (Hünig base) were refluxed in 20 mL of dichloromethane for 2 hours, then another 1 mL of Hünig base and 0.5 g of Meerwein salt were added and the mixture was refluxed again for 2 hours. After cooling, the mixture was extracted 3× with water, and the organic phase was dried over MgSO4 and evaporated down to the residue. Yield: 1.05 g of crude.

Workup

  1. temperaturethe mixture was refluxed again for 2 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted 3× with water
  4. dry with materialthe organic phase was dried over MgSO4
  5. customevaporated down to the residue

Sources & evidence

ORD record
ord-66d59347ea764f65b11e14bc8b06443d
Source dataset
uspto-grants-2010_05
Patent number
US07723381B2

Reaction notes

Loading…