Triethylamine → HCID 57311014, compound

HRID 863185Notes

Reaction equation

HRID 863185 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][C@@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:4]([CH2:17][OH:18])=[CH:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:18][CH2:17][C:4]1[C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:6][CH2:7][C@H:2]([CH3:1])[CH:3]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57206874HCID 57206874, compound

Product 1

HCID 57311014HCID 57311014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2S,5R)-(5,6-dihydro-5-methyl-2-nonyl-2H-pyran-3-yl)methanol (10 mg) and triethylamine (17 ml) in dry dichloro-methane (0.5 ml) was added methanesulfonyl chloride (10 ml) at 0° C. The mixture was allowed to warm to room temperature, and stirred for 30 min. The reaction was quenched by the addition of aqueous saturated sodium bicarbonate solution. The resulting mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the residue by preparative thin layer chromatography gave (2S,5R)-(5,6-dihydro-5-methyl-2-nonyl-2H-pyran-3-yl)methyl methanesulfonate (100 mg).

Workup

  1. customThe reaction was quenched by the addition of aqueous saturated sodium bicarbonate solution
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by preparative thin layer chromatography

Sources & evidence

ORD record
ord-4e8114a300974711a24e586d71cee718
Source dataset
uspto-grants-1998_02
Patent number
US05719291

Reaction notes

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