Water → Non-8-en-1-ol

HRID 1858875Notes

Reaction equation

HRID 1858875 reaction equation
C(N([CH2:6][CH3:7])CC)C.[CH3:8]S(Cl)(=O)=O.[OH2:13].[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[CH2:14]([OH:13])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:8][CH:6]=[CH2:7]

Participants

5

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 11094728Non-8-en-1-olYield 95%

Procedure

A solution of 0.064 mole of 8-nonen-1-ol and 0.19 mole of triethylamine (3 molar excess) in 100 mL of hexane was prepared. To the stirred solution, 0.13 mole of methanesulfonyl chloride (2 molar excess) was added dropwise over 5 min. After the addition was complete, stirring was continued for 2 h. Cold water was poured into the reaction mixture to destroy any excess methanesulfonyl chloride. The aqueous layer was separated from the organic layer, and was extracted with diethyl ether. The organic phases were combined and washed with dilute HC, H2O, 5% NaHCO3 and H2O. The organic layer was dried over MgSO4 and the solvent was removed by rotary evaporation. The respective reactions afforded 8-nonen-1-mesylate in 95% yield. The final product had the following properties: 1H NMR (300 MHZ, CDCl3): δ 5.86-5.72 (m, 1H), 5.02-4.91 (m, 2H), 4.23 (t, J=7.4 Hz, 2H), 2.97 (s, 2H), 2.05 (m, 2H), 1.80 (m, 2H), 1.39-1.27 (m, 8H). 13C NMR (75.5 MHZ, CDCl3): δ 138.33, 113.78, 69.85, 36.52, 33.19, 28.59, 28.35 (2 peaks), 28.23, 24.86.

Workup

  1. additionAfter the addition
  2. customto destroy any excess methanesulfonyl chloride
  3. customThe aqueous layer was separated from the organic layer
  4. extractionwas extracted with diethyl ether
  5. washwashed with dilute HC, H2O, 5% NaHCO3 and H2O
  6. dry with materialThe organic layer was dried over MgSO4
  7. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-c38b3447b5fe414598e7ef597ca19ee0
Source dataset
uspto-grants-2000_11
Patent number
US06153322

Reaction notes

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