Water → HCID 12992837, compound

HRID 1610946Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].O>C(OCC)(=O)C>[CH3:8][S:9]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:23][CH:22]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (32.9 ml) and methanesulfonyl chloride (14.6 ml) were added to a solution of 4-(4-tert-butoxyphenyl)butan-1-ol (35.0 g) in ethyl acetate (360 ml) at 0° C., and the mixture was stirred at 0° C. for 1.5 hr. By adding water, the reaction mixture was separated. The organic layer was washed successively with 5% sodium hydrogen carbonate solution and water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crude 4-(4-tert-butoxyphenyl)butyl methanesulfonate (50.2 g). A suspension of the product (50.2 g) and sodium iodide (46.1 g) in acetone (500 ml) was stirred for 4.5 hr. By adding water and diisopropyl ether, the reaction mixture was separated. The organic layer was successively washed with 10% hypo-water and water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the titled compound (52.1 g) as a colorless oil.

Workup

customthe reaction mixture was separated
washThe organic layer was washed successively with 5% sodium hydrogen carbonate solution and water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-54830a38410e461399b0247845bc20a0
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06984653B2

Reaction notes

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