Triethylamine → 7-(Phenyloxy)-1-heptyl methanesulfonate

HRID 2086544Notes

Reaction equation

HRID 2086544 reaction equation
[C:1]1([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][S:17]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 158562647-(Phenyloxy)-1-heptanol

Product 1

HCID 227239427-(Phenyloxy)-1-heptyl methanesulfonateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7-(phenyloxy)-1-heptanol (0.21 g, 1.01 mmol) in anhydrous methylene chloride (20 mL), taken in a 50 mL round bottomed flask was cooled to 0° C. using an ice bath. Methanesulfonyl chloride (0.177 g, 1.55 mmol) was added to this followed by a dropwise addition of triethylamine (0.28 mL, 2.11 mmol). The reaction mixture was then stirred at 0° C. for 1 hour and allowed to attain room temperature in 2 hours. It was then quenched with 1N. HCl (10 mL) and diluted with methylene chloride (20 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (2×10 mL). The combined organic layer was washed with 1N. HCl (3×10 mL), water (2×10 mL) and brine (2×mL). The organic layer was dried over Na2SO4. Removal of solvent from the dried extract under reduced pressure afforded the product 7-(phenyloxy)-1-heptyl methanesulfonate (0.25 g, 86.5%). The product from the step B was analyzed yielding the following confirmatory data: 1H-NMR (CDCl3) 1.31-1.52 (m, 6H), 1.71-1.84 (m, 4H), 2.98 (s, 3H), 3.94 (t, 2H, J=6.43 Hz), 4.21 (t, 2H, J=6.51 Hz), 6.80-6.94 (m, 3H) and 7.24-7.30 (m, 2H); 13C-NMR (CDCl3) 25.2, 25.7, 28.6, 28.9, 29.0, 37.1, 67.5, 69.9, 114.3, 120.3, 129.2 and 158.9; IR (neat): 1349 cm−1; MS (ES+): 287 (M+1).

Workup

  1. waitto attain room temperature in 2 hours
  2. customIt was then quenched with 1N
  3. additionHCl (10 mL) and diluted with methylene chloride (20 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with methylene chloride (2×10 mL)
  6. washThe combined organic layer was washed with 1N
  7. dry with materialThe organic layer was dried over Na2SO4
  8. customRemoval of solvent from the dried
  9. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-3de6c356a8f9409294081a9bd8372802
Source dataset
uspto-grants-2004_04
Patent number
US06727237B2

Reaction notes

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