Triethylamine → HCID 57311014, compound

HRID 2399579Notes

Reaction equation

HRID 2399579 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 (10.0 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-7737d497f8e143cba40d114edd205c55
Source dataset
uspto-grants-1995_09
Patent number
US05449785

Reaction notes

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