Water → 1,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

HRID 595234Notes

Reaction equation

C(N(CC)CC)C.[O:8]1[C:12]2([CH2:17][CH:16](O)[CH2:15][CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].[OH2:24]>ClCCl>[CH3:19][S:20]([O:22][CH:15]1[CH2:16][CH2:17][C:12]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:13][CH2:14]1)(=[O:24])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (2.4 mL, 17 mmol) was added to a solution of 1,4-dioxaspiro[4,5]decan-9-ol (884 mg, 5.59 mmol) in dichloromethane (22 mL) under a nitrogen atmosphere. The solution was cooled to 0° C. in an ice bath. Methanesulfonyl chloride (0.87 mL, 11.2 mmol) was added and the reaction stirred for 4 h while warming up to room temperature. Water was added and the mixture was extracted with dichloromethane (2×). The combined organic layers were washed with brine (1×), dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexane) to afford 1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate as a light yellow oil. 1H NMR (500 MHz, DMSO-d6) δ 4.81-4.68 (m, 1H), 3.91-3.78 (m, 4H), 3.16 (s, 3H), 1.87 (ddd, J=4.2, 8.1, 16.6, 2H), 1.82-1.71 (m, 2H), 1.67 (ddd, J=4.3, 7.9, 12.3, 2H), 1.58 (ddd, J=4.8, 8.7, 13.3, 2H).

Workup

temperaturewhile warming up to room temperature
extractionthe mixture was extracted with dichloromethane (2×)
washThe combined organic layers were washed with brine (1×)
dry with materialdried with magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexane)

Sources & evidence

ORD record: ord-f02c5bf3c4894c50b2a8964380aaf68a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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