Methanesulfonyl chloride → HCID 86717502, compound

HRID 712049Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[C@H:4]([O:12][CH3:13])[CH2:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>ClCCl>[CH3:13][O:12][C@@H:4]1[CH2:3][C@H:2]([O:1][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:7][CH2:6][C@@H:5]1[C:8]([O:10][CH3:11])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl (1S,2R,4R)-4-hydroxy-2-methoxycyclohexanecarboxylate (racemic) (1.14 g, 6.06 mmol) in dichloromethane (30 mL) was treated with methanesulfonyl chloride (0.938 mL, 12.1 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 2 h and partitioned between ethyl acetate and water. The organic phase was concentrated and purified on silica gel (eluting with 50% ethyl acetate in hexanes) to give the desired product (1.48 g, 93%). 1H NMR (400 MHz, CDCl3) δ 4.89 (1H, m), 3.70 (3H, s), 3.62 (1H, m), 3.36 (3H, s), 3.02 (3H, s), 2.78 (1H, m), 2.42 (1H, m), 2.01 (2H, m), 1.98 (1H, m), 1.80 (1H, m), 1.62 (1H, m) ppm.

Workup

custompartitioned between ethyl acetate and water
concentrationThe organic phase was concentrated
custompurified on silica gel (eluting with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-4108df3015fe473aa2cf5bbf289e9105
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

Loading…