Triethylamine → HCID 58248246, compound

HRID 2280626Notes

Reaction equation

HRID 2280626 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>ClCCl>[CH3:14][S:15]([O:6][C@@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 641512(-)-3-Hydroxytetrahydrofuran

Product 1

HCID 58248246HCID 58248246, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-Tetrahydrofuran-3-ol 1a (300 mg, 3.40 mmol) and triethylamine (687 mg, 6.80 mmol) were dissolved in 20 mL of dichloromethane in an ice bath, followed by addition of methanesulfonyl chloride (468 mg, 4.10 mmol). The reaction solution was warmed up to room temperature and stirred for 2 hours. The reaction solution was mixed with 10 mL of dichloromethane, washed with water (30 mL×3), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (R)-tetrahydrofuran-3-yl methanesulfonate 1b (520 mg) as a yellow oil, which was directly used in the next step without further purification.

Workup

  1. washwashed with water (30 mL×3)
  2. dry with materialdried with anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4586a53b8a354e42b08b54f65c7fdc4e
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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