Dichloromethane → HCID 53903505, compound

HRID 1067115Notes

Reaction equation

HRID 1067115 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]([OH:11])=[O:10].[C:12]1([C:18]([CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)O)=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.ClCCl.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]([O:11][CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:19])=[O:10]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8400Benzoin2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109207542-Oxocyclohexylacetic acid

Product 1

HCID 53903505HCID 53903505, compoundYield 126.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2-oxocyclohex-1-yl)acetic acid (5.6 g), benzoin (7.4 g), 4-dimethylaminopyridine (0.42 g) and dichloromethane (60 ml), 1-ethyl-3-(3'-dimethylaminopropyl)-carbodiimide hydrochloride (8.7 g) was added in ice-water bath. After the reaction mixture was raised to room temperature, N,N-dimethylformamide (10 ml) was added to dissolve benzoin and stirred overnight. After usual workup, 1,2-diphenyl-2-oxoethyl (2-oxocyclohex-1-yl)acetate (15.5 g) was obtained as a crude solid.

Sources & evidence

ORD record
ord-d38e018cc14e4d8eaec5b6c01fd4fa35
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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