m-Chloroperbenzoic acid → HCID 86599514, compound

HRID 2221352Notes

Reaction equation

HRID 2221352 reaction equation
C(=O)([O-])[OH:2].[Na+].[CH3:6][C:7]1([CH3:31])[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:17][C:18]([NH:20][CH:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23][CH2:22]3)=[O:19])[CH:13]=2)[O:8]1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[CH3:6][C:7]1([CH3:31])[CH:16]2[O:2][CH:15]2[C:14]2[CH:13]=[C:12]([CH2:17][C:18]([NH:20][CH:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23][CH2:22]3)=[O:19])[CH:11]=[CH:10][C:9]=2[O:8]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 69062509HCID 69062509, compound

Product 1

HCID 86599514HCID 86599514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

950 ml of a saturated aqueous sodium hydrogen carbonate solution was added to a solution of 11 g of the 2-(2,2-dimethyl-2H-chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide obtained above in 600 ml dichloromethane. A total of 15 g m-chloroperoxybenzoic acid (=MCPBA) in three 5 g portions was added to this receiving solution at 5 min. intervals, and the mixture was stirred for 18 hours at room temperature. The organic phase was separated and substantially entirely evaporated on a rotary evaporator at 65° C. and 20 bar. 2-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide was obtained as crude oil, which was used without further purification for the subsequent reaction.

Workup

  1. customThe organic phase was separated
  2. customsubstantially entirely evaporated on a rotary evaporator at 65° C.

Sources & evidence

ORD record
ord-7e0e9f46242d459fbf7cc373f131cf5e
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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