Dicyclohexylcarbodiimide → HCID 86698886, compound

HRID 76236Notes

Reaction equation

HRID 76236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]([OH:20])=[O:19])[CH2:17][CH2:16]3)=[CH:11][C:10]=2[F:21])[CH:5]=[CH:6][C:7]=1[Cl:8].C1(N=C=NC2CCCCC2)CCCCC1.[O:37]1[CH2:39][CH:38]1[CH2:40]O>C(Cl)Cl>[O:37]1[CH2:39][CH:38]1[CH2:40][O:19][C:18]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[C:10]([F:21])[CH:11]=2)[CH2:17][CH2:16]1)=[O:20]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11164GlycidolHCID 9996409Chf-5074

Product 1

HCID 86698886HCID 86698886, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3′,4′-Dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarboxylic acid (2.00 g, 6.15 mmol), dicyclohexylcarbodiimide (DCC, 2.54 g, 12.30 mmol), 4-dimethyl-aminopyridine (DMAP, 0.075 g, 0.614 mmol), and oxiran-2-ylmethanol (0.490 ml, 7.38 mmol) were dissolved in dry DCM (40 mL). The reaction mixture was stirred at room temperature (r.t.) overnight, then it was filtered and the filtrate was evaporated to dryness to afford 4.4 g of crude. The crude was purified by gradient flash chromatography eluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v) to afford 1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid oxiranylmethyl ester (1.0 g, 42.6% yield).

Workup

  1. filtrationit was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto afford 4.4 g of crude
  4. customThe crude was purified by gradient flash chromatography
  5. washeluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v)

Sources & evidence

ORD record
ord-adf76516f8b940948a53a132b73a1d44
Source dataset
uspto-grants-2014_09
Patent number
US08835494B2

Reaction notes

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