Water → HCID 18760350, compound

HRID 1943083Notes

Reaction equation

HRID 1943083 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][CH2:13][C:14]#[C:15][CH2:16][OH:17].O.[Na+].[Cl-]>C(Cl)Cl>[S:2]([O:17][CH2:16][C:15]#[C:14][CH2:13][O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)(=[O:4])(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chlorideHCID 111233154-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

Product 1

HCID 18760350HCID 18760350, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.0 mL, 12.80 mmol) was added dropwise to a stirred solution of 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (1.9232 g, 11.30 mmol) and TEA (2.5 mL, 17.85 mmol) in DCM (40 mL) at ° C. for five minutes. And then the resulting mixture was stirred at room temperature for 5.5 hours. Water (20 mL) was added, followed by addition of saturated aqueous NaCl solution (70 mL). The organic phase was separated and washed again with brine (60 mL), dried over Na2SO4, concentrated. The residue was separated by flash column chromatography on silica gel using 5-25% EtOAc/hexane to afford 1.542 g of product (yield 55%, oil), along with 400 mg of Di-4-(tetrahydro-pyran-2-yloxy)-but-2-ynyl ether (yield 22%). 1H-NMR (CDCl3): δ 4.88 (t, J=1.8 Hz, 2 H), 4.76 (t, J=3.0-3.3 Hz, 1 H), 4.37-4.24 (m, 2 H), 3.80-3.76 (m, 1 H), 3.54-3.50 (m, 1 H), 3.11 (s, 3 H), 1.78-1.51 (m, 6 H).

Workup

  1. customThe organic phase was separated
  2. washwashed again with brine (60 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was separated by flash column chromatography on silica gel using 5-25% EtOAc/hexane

Sources & evidence

ORD record
ord-d8f0158c39164b51bdd4c803e1d7218a
Source dataset
uspto-grants-2013_03
Patent number
US08389759B2

Reaction notes

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