Methanesulfonyl chloride → (1RS,2RS,3RS)-2-Methanesulfonyloxymethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

HRID 863160Notes

Reaction equation

HRID 863160 reaction equation
[OH:1][CH2:2][CH:3]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH2:21][O:22][CH3:23])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:24][CH2:25][CH2:26][CH3:27])[CH:9]=2)[CH:4]1[C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[CH3:37][S:38]([O:1][CH2:2][CH:3]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH2:21][O:22][CH3:23])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:24][CH2:25][CH2:26][CH3:27])[CH:9]=2)[CH:4]1[C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)(=[O:40])=[O:39]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 21714799(1RS,2RS,3RS)-2-Hydroxymethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

Product 1

HCID 21714794(1RS,2RS,3RS)-2-Methanesulfonyloxymethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1RS,2RS,3RS)-2-hydroxymethyl-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (1.388 g, 2.82 mmol) in methylene chloride (10 ml) with TEA (1.2 ml) stirred under argon at 0° C. was added methanesulfonyl chloride (0.41 g, 3.5mmol). The cooling bath was removed and stirring continued for 1 h. The mixture was partitioned between EtOAc and 3N HCl. The organic extract was washed with H2O, saturated NaHCO3 solution, H2O, then brine, dried (Na2SO4) and solvent removed in vacuo to afford the title compound as an oil (1.52 g, 95%).

Workup

  1. customThe cooling bath was removed
  2. customThe mixture was partitioned between EtOAc and 3N HCl
  3. extractionThe organic extract
  4. washwas washed with H2O, saturated NaHCO3 solution, H2O
  5. dry with materialbrine, dried (Na2SO4) and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-4d03d9ba2ced454286513056a8168d8b
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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