Dimethylamine → HCID 22731316, compound

HRID 2085603Notes

Reaction equation

HRID 2085603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([OH:17])=O)[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(C(Cl)(Cl)Cl)=O.[CH3:47][NH:48][CH3:49].O1CCCC1>C1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([N:48]([CH3:49])[CH3:47])=[O:17])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8303HexachloroacetoneHCID 11776TriphenylphosphineHCID 22731315HCID 22731315, compound2×

Product 1

HCID 22731316HCID 22731316, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (−78° C.) solution of 3-(5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-propionic acid (Intermediate 77, 0.7 g, 2.34 mmol) and triphenyl phosphine (0.74 g, 2.81 mmol) in anhydrous benzene (10 mL) and dichloromethane (20 mL) was treated with hexachloroacetone (0.178 mL, 1.17 mmol). After 1 h, a 2M solution of dimethyl amine in tetrahydrofuran (3 mL, 6 mmol) was added. After 1 h, the reaction mixture was evaporated in vacuo to a brown oil which was subjected to flash column chromatography using 40% ethyl acetate in hexane as the eluent to afford the title compound (0.65 g, 84%).

Workup

  1. waitAfter 1 h
  2. customthe reaction mixture was evaporated in vacuo to a brown oil which

Sources & evidence

ORD record
ord-93c76a0c81724ea7bb0b090d46e559e1
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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