Ethyl Lactate → HCID 54142872, compound

HRID 2253719Notes

Reaction equation

HRID 2253719 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([OH:22])(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH:44]([CH3:47])[CH2:45]O)=[C:39]([F:48])[C:38]=2[F:49])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(OCC)(=O)C(C)O.[Li+].[BH4-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH:44]([CH3:45])[CH2:47][O:21][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[C:39]([F:48])[C:38]=2[F:49])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 5

HCID 7344Ethyl LactateHCID 7991Pentanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 4148881Lithium borohydrideHCID 19745626HCID 19745626, compound

Product 1

HCID 54142872HCID 54142872, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 0.1 mol of DCC, dissolved in methylene chloride, is added with exclusion of moisture to a mixture of 0.1 mol of pentanoic acid, 0.1 mol of optically active 2-(4'-heptyloxy-2,3-difluorobiphenyl-4-oxy)propan-1-ol (prepared by reduction of the corresponding ethyl lactate using LiBH4) and a catalytic amount of DMAP in 250 ml of methylene chloride. The mixture is subsequently stirred at room temperature for 12 hours, the precipitate is filtered off with suction, and the filtrate is worked up in a customary manner, to give optically active 4'-heptyloxy-2,3-difluoro-4-(1-valeroyloxy-2-propyloxy)biphenyl.

Workup

  1. filtrationthe precipitate is filtered off with suction

Sources & evidence

ORD record
ord-20eb0ff0ebc1463aadc33f64a34d025f
Source dataset
uspto-grants-1993_08
Patent number
US05232624

Reaction notes

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