Tetrabutylammonium Fluoride → HCID 14713770, compound

HRID 2115938Notes

Reaction equation

HRID 2115938 reaction equation
C([Si]([O:8][CH2:9][CH:10]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:12]=2[O:11]1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[CH3:20][O:19][C:18]1[C:12]2[O:11][CH:10]([CH2:9][OH:8])[CH2:14][C:13]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68966264HCID 68966264, compound

Product 1

HCID 14713770HCID 14713770, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-tert-butyl[(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methoxy]dimethylsilane (34.12 g; 0.116 mol) in tetrahydrofuran (700 mL) cooled to 0° C. was added via an addition funnel tetrabutylammonium fluoride (140 mL, 1.0 M solution in tetrahydrofuran) and the reaction mixture was allowed to stir at room temperature for 6 h. The reaction was diluted with water (500 mL) and extracted with ethyl acetate (2×300 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give (±)-(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanol, a crude oil. The alcohol was dissolved in dichloromethane (700 mL) and p-toluenesulfonyl chloride (33.14 g, 0.174 mol) was added followed by triethylamine (21.11 g, 0.209 mol) and then 4-(dimethylamino)pyridine (2.12 g, 0.017 mol). The reaction mixture was allowed to stir at 50° C. for 12 h. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7) provided 26.45 g (68%) of (±)-(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white crystalline solid. Rf=0.38 (silica, ethyl acetate:hexanes 3:7); mp 98-103° C.; Anal. calcd. for C17H18O5S: C, 61.06; H, 5.43. Found: C, 60.80; H, 5.37.

Workup

  1. extractionextracted with ethyl acetate (2×300 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride (400 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-36f7213ae0844c4c9d1ae08404e647dd
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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