4-Toluenesulfonyl chloride → 1,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

HRID 1505681Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:12]1[C:16]2([CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1>N1C=CC=CC=1>[O:12]1[C:16]2([CH2:21][CH2:20][CH:19]([O:22][S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 5 °C

Procedure

4-Methyl-benzenesulfonyl chloride (5.51 g; 29 mmol; 1.0 eq.) was added portionwise to a solution of 1,4-Dioxa-spiro[4.5]decan-8-ol (4.44 g; 28 mmol; 1.0 eq.) in anhydrous Pyridine (13.5 mL) maintained at 5° C. with an ice bath. The reaction mixture was then allowed to warm to RT and stirred O/N. It was then quenched by addition of water and diluted with EtOAc. Organic phase was washed with a 1N HCl solution, saturated NaHCO3 solution and brine. It was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 6.9 g of a pale yellow oil. Purification by flash chromatography on silica (heptane/EtOAc 60:40) afforded the title compound as a white powder (4.7 g, 52%). HPLC (Condition A): Rt 4.04 min (purity 100%). MS (ESI+): 330.3

Workup

temperatureto warm to RT
customIt was then quenched by addition of water
additiondiluted with EtOAc
washOrganic phase was washed with a 1N HCl solution, saturated NaHCO3 solution and brine
dry with materialIt was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8b3a1fd60e62461daf0c9aa54d88a323
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216991B2

Reaction notes

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