Water → 7-Methanesulfonyl-1-heptene

HRID 1954110Notes

Reaction equation

HRID 1954110 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C.O>ClCCl>[CH3:9][S:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 543123Hept-6-en-1-ol

Product 1

HCID 232958707-Methanesulfonyl-1-hepteneYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

This example illustrates a synthesis of 1-(6,7-Oxidoheptyl)-3,7-dimethylxanthine (inventive compound no. 1586). To a solution of 6-hepten-1-ol (6.00 g, 52.6 mmol) in dichloromethane (120 mL) at 0° C. was added methanesulfonyl chloride (6.07 g, 4.0 mL, 53.0 mmol), followed by triethylamine (7.79 g, 77.0 mmol). After stirring for 10 minutes at 0° C., the reaction was allowed to warm to 25° C. and then stirred for 2 hours. The reaction was poured into water (100 mL) and extracted with dichloromethane (2×100 mL). The organic portions were combined, dried over magnesium sulfate, and evaporated to give the 7-methanesulfonyl-1-heptene as a yellow oil (9.30 g, 93%), which was used without further purification.

Workup

  1. temperatureto warm to 25° C.
  2. stirringstirred for 2 hours
  3. extractionextracted with dichloromethane (2×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b621db91c977476d9a5b1f173f27672c
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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