Water → 1-methanesulfonyl-4-(S)-methyl-8-methylnon-7-ene

HRID 361536Notes

Reaction equation

HRID 361536 reaction equation
[CH3:1][C@@H:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:3][CH2:4][CH2:5]O.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.O>ClCCl>[CH3:13][S:14]([CH2:5][CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111712294-(S)-methyl-8-methylnon-7-enyl alcohol

Product 1

HCID 228614901-methanesulfonyl-4-(S)-methyl-8-methylnon-7-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(S)-methyl-8-methylnon-7-enyl alcohol (3.25 g, 19.1 mmol) in dichloromethane (50 mL) at 0° C. is added methanesulfonyl chloride (2.29 g, 20.0 mmol) followed by triethylamine (3.04 g, 30.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and stirred for 3 hours. The reaction was poured into water (50 mL), separated and washed with dichloromethane (50 mL). The organic portions were combined, dried using magnesium sulfate, and evaporated to give the 1-methanesulfonyl-4-(S)-methyl-8-methylnon-7-ene as a yellow oil which is used without further purification.

Workup

  1. temperatureto warm to 25° C.
  2. stirringstirred for 3 hours
  3. customseparated
  4. washwashed with dichloromethane (50 mL)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-becf6b43835c44448df7784a0191eda9
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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