Triethylamine → HCID 18790079, compound

HRID 1107160Notes

Reaction equation

HRID 1107160 reaction equation
[OH:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([O:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18790064HCID 18790064, compound

Product 1

HCID 18790079HCID 18790079, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-hydroxy-2,2-dimethyl-7-phenylheptanoate (10 g, 38 mmol) and triethylamine (6.3 mL, 45 mmol) are dissolved in CH2Cl2 (50 mL) and cooled to 0° C. Methanesulfonyl chloride (3.2 mL, 42 mmol) is added and the reaction is allowed to stir at room temperature for 1 hour. The reaction mixture is then washed with NaHCO3 (2×40 mL), 1 N HCl (40 mL) and brine (40 mL). The solution is dried over MgSO4 and the solvent removed in vacuo to yield methyl 3-methanesulfonyloxy-2,2-dimethyl-7-phenylheptanoate (11.2 g, 86%). 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.19-7.15 (m, 3H), 4.99 (dd, J=9.2, 2.0 Hz,1H), 3.69 (s, 3H), 2.93 (s, 3H), 2.62 (t, J=7.4 Hz, 2H), 1.71-1.38 (m, 6H), 1.27 (s, 3H), 1.18 (s, 3H); MS (FAB) m/e 343 (M+H)+.

Workup

  1. washThe reaction mixture is then washed with NaHCO3 (2×40 mL), 1 N HCl (40 mL) and brine (40 mL)
  2. dry with materialThe solution is dried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cb5f1f4edfa042deb64d2fe70b8712b8
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

Loading…