Solketal → HCID 67520733, compound

HRID 1787059Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.Br[CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[C:19]([Si:16]([O:15][CH2:14][CH2:13][O:10][CH2:9][CH:7]1[CH2:6][O:5][C:4]([CH3:11])([CH3:3])[O:8]1)([CH3:18])[CH3:17])([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

60% Sodium hydride (890 mg) was suspended in N,N-dimethylformamide (60 mL), and the suspension was cooled to 0° C. (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol (2.3 mL) was added dropwise and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added (2-bromoethoxy)(tert-butyl)dimethylsilane (3 mL), and the mixture was stirred at 0° C. for 2 hrs. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=100:0→90:10) to give the title compound (1.04 g) as a yellow oil.

Workup

additionwas added dropwise
stirringthe mixture was stirred at 0° C. for 2 hrs
extractionthe mixture was extracted with ethyl acetate
washThe organic layer washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was separated
custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=100:0→90:10)

Sources & evidence

ORD record: ord-aac7ad5b237b4d34a24963f4d259c78f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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