3-Hydroxy-3-methyl-2-butanone → HCID 22350069, compound

HRID 896660Notes

Reaction equation

HRID 896660 reaction equation
CC(C)([O-])C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:50]1[CH:55]=[CH:54][C:53]([S:56][CH3:57])=[CH:52][CH:51]=1.[OH:58][C:59]([CH3:64])([CH3:63])[C:60](=[O:62])[CH3:61]>C1COCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:58][C:59]([CH3:64])([CH3:63])[C:60](=[O:62])[CH2:61][C:50]1[CH:55]=[CH:54][C:53]([S:56][CH3:57])=[CH:52][CH:51]=1

Participants

8

Reactant 4

HCID 82613-Hydroxy-3-methyl-2-butanoneHCID 660374-BromothioanisoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxide

Product 1

HCID 22350069HCID 22350069, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of sodium tert-butoxide (12 g, 125 mmol), XANTPHOS (2.05 g, 3.5 mmol) and Pd2(dba)3 (1.35 g, 1.5 mmol) in THF (600 mL) was added 4-bromothioanisole (20 g, 98 mmol) and 3-hydroxy-3-methyl-butan-2-one (12 g, 117 mmol). The resulting reaction mixture was heated to 75° C. for 2 h then cooled to r.t. and diluted with water. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 85:15-80:20) provided the title compound as a pale brown solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturethen cooled to r.t.
  3. washThe organic extracts were washed (H2O), (brine),
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washby flash chromatography (eluting with hexane/ethyl acetate, 85:15-80:20)

Sources & evidence

ORD record
ord-22021106c0374a1197fbf8e5a6ebf7c2
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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