Diethyl Ether → HCID 19988333, compound

HRID 973713Notes

Reaction equation

HRID 973713 reaction equation
[C:1]([C:3]1([CH2:22][CH:23]([CH3:26])[CH2:24][CH3:25])[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)#[N:2].CCOCC.[Cl:32][CH:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35].C1CCC(N=C=NC2CCCCC2)CC1>CN1C(=O)CCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:32][CH:33]([CH:37]([CH3:39])[CH3:38])[C:34]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH:6]3[CH2:7][CH2:8][C:3]([C:1]#[N:2])([CH2:22][CH:23]([CH3:26])[CH2:24][CH3:25])[CH2:4][CH2:5]3)=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)=[O:35]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 3134932-chloro-3-methylbutanoic acidHCID 19988315HCID 19988315, compound

Product 1

HCID 19988333HCID 19988333, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5.3 g of p-[p-(4-cyano-4-(2-methylbutyl)-cyclohexyl)-phenyl]-phenol (obtainable by alkaline ether cleavage from r-1-cyano-cis-4-(4'-propyloxybiphenyl-4-yl)-1-(2-methylbutyl)-cyclohexane with potassium tert.-butylate in NMP at 180°), 1.9 g of optically active 2-chloro-3-methyl-butyric acid and 170 g of DMAP are suspended in 40 ml of CH2Cl2. 3.1 g of DCC in 5 ml of CH2Cl2 are then added dropwise and the mixture is stirred at room temperature for 12 hours. After removal of the dicyclohexylurea and customary working up, optically active 4'-(4-cyano-4-(2-methylbutyl)-cyclohexyl)-biphenyl-4-yl 2-chloro-3-methyl-butyrate is obtained.

Workup

  1. customAfter removal of the dicyclohexylurea

Sources & evidence

ORD record
ord-fa4199fae3d749f396dbb5ad342ecade
Source dataset
uspto-grants-1991_11
Patent number
US05064569

Reaction notes

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