Sulfuric Acid → HCID 11579411, compound

HRID 2103029Notes

Reaction equation

HRID 2103029 reaction equation
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:3]=1[CH:4](O)[CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.C1(S(N)(=O)=O)C=CC=CC=1.S(=O)(=O)(O)O>C1COCC1>[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:3]=1[CH:4]=[CH:5][C:6]1([O:10]2)[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7370BenzenesulfonamideHCID 69055644HCID 69055644, compound

Product 1

HCID 11579411HCID 11579411, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol (200 mg) and phenyl sulfonamide (1.35 g) in THF (15 mL) was added dropwise a sulfuric acid solution in THF (2 drops, 98% sulfuric acid, 5 mL THF). The mixture was allowed to stir 30 minutes at 0° C. and then at room temperature for another 30 minutes. The solution was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate (2×10 mL). The combined organic solutions were washed with water and dried over Na2SO4. Upon removal of solvents to dryness, the crude products were purified using flash column chromatography (0-20% ethyl acetate in hexanes) to yield 5,7-dimethylspiro[chromene-2,1′-cyclobutan]-6-ol as an off-white solid (106 mg).

Workup

  1. waitat room temperature for another 30 minutes
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe aqueous phase was washed with ethyl acetate (2×10 mL)
  4. washThe combined organic solutions were washed with water
  5. dry with materialdried over Na2SO4
  6. customUpon removal of solvents to dryness
  7. customthe crude products were purified

Sources & evidence

ORD record
ord-e8f020fb4d6e43f9a5b6d1f12cf28652
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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