Triethylamine → (5,6-dioxo-2,3,5,6-tetrahydronaphtho[1,2-b][1,4]oxathiin-2-yl)methyl Methanesulfonate

HRID 563116Notes

Reaction equation

HRID 563116 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][C:7]2[C:9]3[C:14]([C:15](=[O:18])[C:16](=[O:17])[C:6]=2[S:5][CH2:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:1][CH2:2][CH:3]1[O:8][C:7]2[C:9]3[C:14]([C:15](=[O:18])[C:16](=[O:17])[C:6]=2[S:5][CH2:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 577754892-(Hydroxymethyl)-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione

Product 1

HCID 57775490(5,6-dioxo-2,3,5,6-tetrahydronaphtho[1,2-b][1,4]oxathiin-2-yl)methyl MethanesulfonateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(hydroxymethyl)-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione (1.0 g, 3.81 mmol) in dichloromethane (10 mL) was added triethylamine (1.0 mL, 7.63 mmol) and methanesulfonyl chloride (0.60 mL, 7.63 mmol). The resulting mixture was stirred for 1.5 hours at room temperature. Product was collected by filtration, washed with dichloromethane (10 mL) and dried under reduced pressure to provide the product as a purple solid (1.1 g, 85%). M.p.=230-232° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.89 (d, J=6.8 Hz, 1H), 7.75 (m, 2H), 7.56 (m, 1H), 4.81 (m, 1H), 4.65 (m, 1H), 4.54 (m, 1H), 3.05 (m, 2H), 1.16 (m, 3H); LCMS: 341 [M+H].

Workup

  1. filtrationProduct was collected by filtration
  2. washwashed with dichloromethane (10 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc6152c3b1d94e7980d61d5c0400ab20
Source dataset
uspto-grants-2011_11
Patent number
US08067459B2

Reaction notes

Loading…