Water → HCID 54526121, compound

HRID 1532183Notes

Reaction equation

HRID 1532183 reaction equation
O1CCCCC1[O:7][CH:8]([CH3:23])[C:9]#[C:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+].O>CO.[Cl-].[Na+].O>[OH:7][CH:8]([CH3:23])[C:9]#[C:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[O:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 69961114HCID 69961114, compound

Product 1

HCID 54526121HCID 54526121, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

trans-2-(3-Tetrahydropyranyloxy-but-1-ynyl)-5-(4-fluorophenyl)tetrahydrofuran (204, 280 mg, 0.9 mmol) was dissolved in methanol (15 mL). To this solution was added p-toluenesulfonic acid (50 mg) and the resulting solution was stirred for 45 minutes. Saturated sodium bicarbonate solution (10 mL) was added. After 5 minutes of stirring, the solution was added to 10 mL of water, diluted with 15 mL of brine and extracted with methylene chloride (3×30 nL). The combined organics were dried over sodium sulfate and the solvent was removed via rotary evaporator to yield 212 mg (100%) of trans-2-(3-hydroxy-but-1-ynyl)-5-(4-fluorophenyl) tetrahydrofuran (205). 1H-NMR (CDCl3) 6 7.29 (2H, dd, J=8.7, 5.2 Hz), 7.01 (2H, t, J=8.7 Hz), 5.09 (1H, t, J=7.4 Hz), 4.92 (1H, t, J=7.4 Hz), 4.59 (1H, q, J=6.6 Hz), 2.30-2.50 (2H, in), 2.05-2.15 (1H, m), 2.00 (1H, br s), 1.75-1.88 (1H, m), 1.47 (3H, d, J=6.6 Hz).

Workup

  1. stirringAfter 5 minutes of stirring
  2. extractionextracted with methylene chloride (3×30 nL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. customthe solvent was removed via rotary evaporator

Sources & evidence

ORD record
ord-b30fac7c51344df2a0d7d3b07e43f8b4
Source dataset
uspto-grants-2001_03
Patent number
US06201016B1

Reaction notes

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