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

HRID 1421081Notes

Reaction equation

HRID 1421081 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl.O>[CH3:19][S:20]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of the alcohol from Step 1 (4.59 g, 29 mmol) and triethylamine (8.0 mL, 57 mmol) in dichloromethane (100 mL) was added methanesulfonyl chloride (3.3 mL, 43 mmol). The reaction was then diluted with water (80 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried over MgSO4 and concentrated to give the title compound as a yellow oil.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-70d40bd266344f3b93e8d4153f924b33
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

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