Benzenesulfinic acid → Furan, tetrahydro-2-(phenylsulfonyl)-

HRID 719982Notes

Reaction equation

HRID 719982 reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.[C:6]1([S:12]([OH:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[C:6]1([S:12]([CH:5]2[CH2:4][CH2:3][CH2:2][O:1]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 12057Benzenesulfinic acidHCID 709342,3-Dihydrofuran

Product 1

HCID 10998330Furan, tetrahydro-2-(phenylsulfonyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,3-dihydrofuran (1.40 g, 19.97 mmol) and benzene sulfinic acid (3.12 g, 21.97 mmol) in methylene chloride (80 mL) was stirred at 25° C. for 2 h. The reaction was then transferred to a separatory funnel and washed with a saturated aqueous sodium carbonate solution (15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was then recrystallized using diethyl ether/petroleum ether to afford 2-benzenesulfonyl-tetrahydro-furan as a white solid: mp 55.9–56.8° C.

Workup

  1. customThe reaction was then transferred to a separatory funnel
  2. washwashed with a saturated aqueous sodium carbonate solution (15 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was then recrystallized

Sources & evidence

ORD record
ord-0c4b9590061042fba617b09dd9b2656b
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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