2-Mercaptoethanol → HCID 178470664, compound

HRID 545121Notes

Reaction equation

HRID 545121 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2[C:43]3[O:42]C4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)[C:34]=3C=CC=2)C=CC=CC=1.C(O)C[SH:67]>O1CCOCC1.O>[CH2:12]([O:11][C:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:34][C:43]([OH:42])=[S:67])=[CH:3][CH:4]=1)=[O:10])[CH3:13]

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 178470664HCID 178470664, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 4-bromophenylacetate (500 mg), diisopropylethylamine (700 μL), tris(dibenzylidenacetone)dipalladium(0) (46 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (58 mg) were dissolved in dioxane (5 mL). Then, thioglycol acid (140 μL) was added, and the mixture was heated under reflux for 4 hrs. The reaction mixture was poured into water, the aqueous phase was washed with ethyl acetate and acidified with 1 mol/L hydrochloric acid. Then, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (260 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. washthe aqueous phase was washed with ethyl acetate
  4. extractionThen, and the mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c400cb799400442c9a033dffa22f4edf
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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