Propylene Oxide → 4'-Heptyloxy-2,3-difluoro-4-(2-valeroyloxypropyl)biphenyl

HRID 2253718Notes

Reaction equation

HRID 2253718 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]([CH2:43][CH:44](O)[CH3:45])=[C:39]([F:47])[C:38]=2[F:48])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(OC1C=CC(C2C=CC=C(F)C=2F)=CC=1)CCCCCC.C1OC1C>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]([CH2:43][CH:44]([O:21][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:45])=[C:39]([F:47])[C:38]=2[F:48])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 5

HCID 6378Propylene OxideHCID 7991Pentanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 191036002,3-Difluoro-4'-heptyloxybiphenylHCID 570678764'-Heptyloxy-2,3-difluoro-4(2-hydroxypropyl) biphenyl

Product 1

HCID 145121694'-Heptyloxy-2,3-difluoro-4-(2-valeroyloxypropyl)biphenyl

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 4'-heptyloxy-2,3-difluoro-4(2-hydroxypropyl) biphenyl [sic] (which can be prepared by customary metallation of 4'-heptyloxy-2,3-difluorobiphenyl and reaction with optically active propylene oxide) and a catalytic amount of DMAP in 200 ml of methylene chloride. When the addition is complete, the mixture is stirred at room temperature for 12 hours, the precipitate is filtered off with suction, and the product is worked up in a customary manner. The product is purified by chromatography, to give optically active 4'-heptyloxy-2,3-difluoro-4-(2-valeroyloxypropyl)biphenyl.

Workup

  1. additionWhen the addition
  2. filtrationthe precipitate is filtered off with suction
  3. customThe product is purified by chromatography

Sources & evidence

ORD record
ord-02bc538930974081b020a333345ec973
Source dataset
uspto-grants-1993_08
Patent number
US05232624

Reaction notes

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