Triethylamine → HCID 20645039, compound

HRID 323768Notes

Reaction equation

HRID 323768 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][OH:19])[C:9]=2[CH2:8][CH2:7]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:19][CH2:18][C@@H:16]1[CH2:17][C@@H:15]1[C:14]1[C:9]2[CH2:8][CH2:7][O:6][C:10]=2[CH:11]=[CH:12][CH:13]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53689601HCID 53689601, compound

Product 1

HCID 20645039HCID 20645039, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methane sulfonyl chloride (6.5 mmol) was added dropwise to a solution of (cis)-2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl methanol (5.0 mmol) and triethylamine (7.5 mmol) in 50 mL of CH2Cl2 at 0° C. The resulting mixture was allowed to warm to RT and stirred for 2 h. The crude reaction mixture was then diluted with CH2Cl2 (50 mL) and washed sequentially with water (2×50 mL), saturated aqueous sodium bicarbonate solution (2×50 mL) and then brine (1×50 mL). The organic phase was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 1.38 g of the desired product as an oil (quantitative yield).

Workup

  1. customThe crude reaction mixture
  2. washwashed sequentially with water (2×50 mL), saturated aqueous sodium bicarbonate solution (2×50 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0488c9a31733477e905f6033681c1c7b
Source dataset
uspto-grants-2001_04
Patent number
US06214869B1

Reaction notes

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