HCID 19105562, compound → HCID 19105565, compound

HRID 373418Notes

Reaction equation

HRID 373418 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:5]=2[C:6]([CH3:9])([CH3:8])[CH:7]=1.CC1C2C=C(Br)C=CC=2SC(C)=C1C.[H][H]>C(OCC)(=O)C.[Pd]=S>[CH3:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]2[C:4](=[CH:13][CH:12]=[C:11]([Br:14])[CH:10]=2)[S:3]1

Participants

6

Reactant 3

HCID 19105562HCID 19105562, compoundHCID 19105566HCID 19105566, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19105565HCID 19105565, compound

Reagents, catalysts & solvents 2

HCID 82926Palladium sulfide (PdS)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg (1.9 mmol) of 2,4,4-trimethyl-6-bromo-(4H)-1-benzothiopyran (Compound 50) in 5 ml of ethyl acetate was treated with 500 mg of 10% palladium sulfide on carbon and then shaken under an atmosphere (30 psi) of hydrogen in a Parr apparatus for 24 hours. The mixture was filtered through celite and the solvent was removed in-vacuo. The residue was purified by flash chromatography (silica; hexanes) to give the title compound as a colorless oil. PMR (CDCl3): & 1.21 (3H, s), 1.33 (3H, d, J=6.6Hz), 1.36 (3H, s), 1.64-1.89 (2H, m), 3.37-3.50 (1H, m), 7.10 (1H, dd, J=8.4 Hz, 2.1Hz), 7.19 (1H, d, 8.4 Hz), 7.20 (1H, d, 2.1 Hz)

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was removed in-vacuo
  3. customThe residue was purified by flash chromatography (silica; hexanes)

Sources & evidence

ORD record
ord-99b03c0332214dbdafece52046d652df
Source dataset
uspto-grants-1992_11
Patent number
US05162546

Reaction notes

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