Sodium Carbonate → Ethyl 2-[4-(5-chlorothiophen-2-yl)-phenoxy]-4-cyclohex-1-enylbutanoate

HRID 559070Notes

Reaction equation

HRID 559070 reaction equation
[Cl:1][C:2]1[S:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH2:24][CH2:25][C:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH2:24][CH2:25][C:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=3)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343245-Chlorothiophene-2-boronic acidHCID 66999225Ethyl 2-[(4-bromophenyl)oxy]-4-cyclohex-1-en-1-ylbutanoate

Product 1

HCID 66999601Ethyl 2-[4-(5-chlorothiophen-2-yl)-phenoxy]-4-cyclohex-1-enylbutanoateYield 73%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.18 g (0.04 equivalent) of Pd(PPh3)4 and then 1.2 g (0.0084 mol) of 5-chloro-2-thiopheneboronic acid are added to a solution of 1.4 g (0.0038 mol) of ethyl 2-[(4-bromophenyl)oxy]-4-cyclohex-1-en-1-ylbutanoate in 20 ml of dimethoxyethane. 4.2 ml of 2M sodium carbonate solution are added at room temperature. The reaction mixture is stirred overnight and then refluxed for 2 hours. After cooling to room temperature, the mixture is taken up in water and extracted with ethyl acetate. The extract is washed with 1N sodium hydroxide and then with saturated aqueous NaCl solution and finally dried over Na2SO4. After concentrating, the black oil obtained is purified by flash chromatography (95/5 heptane/ethyl acetate). 1.1 g of a thick oil are obtained.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with 1N sodium hydroxide
  4. dry with materialwith saturated aqueous NaCl solution and finally dried over Na2SO4
  5. concentrationAfter concentrating
  6. customthe black oil obtained
  7. customis purified by flash chromatography (95/5 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-9d41e5168a9843aea2dfe176500b558d
Source dataset
uspto-grants-2011_11
Patent number
US08063067B2

Reaction notes

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