Potassium bisulfate → HCID 18518591, compound

HRID 1369127Notes

Reaction equation

HRID 1369127 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[C:18]([Br:24])[CH:19]=[C:20]([I:23])[CH:21]=2)[C:16]([OH:35])([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[C:15]1=[O:36])(C(C)(C)C)(C)C.OS([O-])(=O)=O.[K+]>C1COCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[C:18]([Br:24])[CH:19]=[C:20]([I:23])[CH:21]=2)[C:16]([OH:35])([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[C:15]1=[O:36]

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 18518560HCID 18518560, compound

Product 1

HCID 18518591HCID 18518591, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(5-t-butyldimethylsilyloxypentyl)-4-bromo-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole (450 mg, 0.67 mmol) in THF (5 mL) was added 1 N n-tetrabutylammonium fluoride in THF (1 mL, 1 mmol) and the mixture was stirred for 4 h at room temperature. 5% KHSO4 was added and the mixture was extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 1:1 to 0:1 hexane/ethyl acetate to give the title compound (349 mg, 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography with 1:1 to 0:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-e945f1c929174a1fa31da28c7bbdb6f3
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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