Carbon Dioxide → HCID 58236465, compound

HRID 1947174Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]=1[O:15][CH2:16][O:17][CH3:18].O1CCCC1.[Li+].CCC[CH2-].[C:29](=[O:31])=[O:30]>O.CCCCCC>[CH:8]([C:6]1[C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]([O:15][CH2:16][O:17][CH3:18])=[C:2]([CH:7]=1)[C:29]([OH:31])=[O:30])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: -60 °C

Procedure

1-bromo-5-isopropyl-2,4-bis-methoxymethoxy-benzene (IM2-a: 12.0 g, 37.8 mmol) and tetrahydrofuran (150 mL) were placed in a 300 mL three-neck flask and cooled to −60° C. To this mixture a hexane solution of N-butyllithium (24 mL, 1.59 M) was added slowly, and after adjusting the temperature of the solution to −40° C. the mixture was stirred for 1 hour. Dry ice powder was added to the reaction mixture and the reaction mixture was allowed to come to room temperature. After completing the reaction, the reaction mixture was mixed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate. After filtration and evaporation, the solid material obtained was purified by suspending in hexane to obtain the title compound (IM3-a: 6.6 g, 62%).

Workup

customto −40° C.
customto come to room temperature
customthe reaction
extractionextracted with ethyl acetate
dry with materialThe extracted organic layer was dried over anhydrous sodium sulfate
filtrationAfter filtration and evaporation
customthe solid material obtained
customwas purified

Sources & evidence

ORD record: ord-958e3b345d384a5cbb1cacd3eb9a872f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399464B2

Reaction notes

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