Sulfuric Acid → HCID 22161962, compound

HRID 1088728Notes

Reaction equation

HRID 1088728 reaction equation
O[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[C:11](O)([CH3:14])([CH3:13])[CH3:12].OS(O)(=O)=O>C1C=CC=CC=1.O>[C:11]([C:3]1[CH:2]=[CH:10][C:6]2[CH2:7][CH2:8][S:9][C:5]=2[CH:4]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 11367101Benzo[b]thiophene-5-ol, 2,3-dihydro-

Product 1

HCID 22161962HCID 22161962, compoundYield 19.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-hydroxy-2,3-dihydrobenzothiophene (500 mg, 3.28 mmoles) in 20 mL benzene in a sealable tube was added t-butanol (729 mg, 9.84 mmoles, 3.0 eq) and 0.4 mL concentrated H2SO4. The tube was sealed and the reaction mixture heated at 60° C. for 24 hours. The reaction mixture was cooled, diluted with water (50 mL) and extracted 2×25 mL ether. The combined extracts were washed with sodium bicarbonate (1×25 mL), H2O (1×25 mL) and brine (1×25 mL). The organic layer was then dried over Na2SO4, filtered and concentrated to give 220 mg crude product. Purification by flash chromatography (90/10, hexane/EtOAc) afforded 125 mg pure product (18%) mp 90°-93° C.

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted 2×25 mL ether
  4. washThe combined extracts were washed with sodium bicarbonate (1×25 mL), H2O (1×25 mL) and brine (1×25 mL)
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 220 mg crude product
  9. customPurification by flash chromatography (90/10, hexane/EtOAc)

Sources & evidence

ORD record
ord-951cb797abb449dcaf093ef3d2ec5d6f
Source dataset
uspto-grants-1990_10
Patent number
US04963580

Reaction notes

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