Diethyl Ether → 2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]thiophene-3-carboxylic acid

HRID 870049Notes

Reaction equation

HRID 870049 reaction equation
Br[C:2]1[C:3]([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([Cl:8])[S:5][C:6]=1[Cl:7].CC[O:26][CH2:27]C.C1C[O:32]CC1>>[Cl:7][C:6]1[S:5][C:4]([Cl:8])=[C:3]([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[C:2]=1[C:27]([OH:26])=[O:32]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 579009842-[(4-bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methoxy]tetrahydro-2H-pyran

Product 1

HCID 579009752,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]thiophene-3-carboxylic acid

Procedure

2-[(4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methoxy]tetrahydro-2H-pyran from Example 8, Step 2 (334 mg, 0.731 mmol) was reacted under conditions similar to Example 1, Step 6 (Et2O was used as a solvent instead of THF; reaction was quenched with 25% aq. NH4OAc instead of 1N HCl). The crude was purified by chromatography on silica gel (50:50 EtOAc/hexane containing 0.25% AcOH) to afford the desired product as a white foam.

Workup

  1. customreaction
  2. customwas quenched with 25% aq. NH4OAc instead of 1N HCl)
  3. customThe crude was purified by chromatography on silica gel (50:50 EtOAc/hexane containing 0.25% AcOH)

Sources & evidence

ORD record
ord-a163734ff2274731bb2c106f3be94af7
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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