Water → 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-6-ene

HRID 337841

Reaction equation

I[C:2]1[C:3]2([CH2:8][CH2:9][CH2:10][CH:11]=1)[O:7][CH2:6][CH2:5][O:4]2.C([Li])CCC.[CH3:17][C:18]1([CH3:29])[C:22]([CH3:24])([CH3:23])[O:21][B:20](OC(C)C)[O:19]1.O>C1COCC1>[CH3:17][C:18]1([CH3:29])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([C:2]2[C:3]3([CH2:8][CH2:9][CH2:10][CH:11]=2)[O:7][CH2:6][CH2:5][O:4]3)[O:19]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 6-iodo-1,4-dioxaspiro[4.5]dec-6-ene (Synlett, 2008, 1086-1090; 2.70 g, 10.2 mmol) in THF (30 mL), butyl lithium (1.65 M solution in hexane; 6.7 mL, 11.1 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 1 hour. Then, 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (4.0 mL, 19.8 mmol) was added thereto, and the mixture was stirred at −78° C. for 2 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1) to yield the title compound (1.52 g, 56%) as a colorless oil.

Workup

stirringthe mixture was stirred at −78° C. for 2 hours
extractionfollowed by extraction with ethyl acetate (50 mL)
dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
concentrationAfter vacuum concentration
customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1)

Sources & evidence

ORD record: ord-beb2518ec90842ddbc94d74f4d5a8283
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889741B2

Linked notes

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