Carbon Dioxide → HCID 68453855, compound

HRID 658104Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][O:11][C:10]([CH3:15])([CH3:14])[O:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:21](=[O:23])=[O:22].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH3:14][C:10]1([CH3:15])[O:9][CH:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[C:21]([OH:23])=[O:22])[CH2:13][CH2:12][O:11]1

Participants

Conditions

Temperature: -78 °C

Procedure

A 1 g portion of 4-(3-bromophenyl)-2,2-dimethyl-1,3-dioxane was dissolved in 18 ml of THF solution and cooled to −78° C., and then 2.35 ml of hexane solution containing 1.57 M n-butyl lithium was added dropwise thereto spending 1 hour. After completion of the dropwise addition, this was further stirred for 30 minutes. After adding excess amount of carbon dioxide thereto at −78° C., the mixture was risen to room temperature. The reaction solution was mixed with ammonium chloride aqueous solution and extracted 10 times with chloroform-methanol (5:1), the organic layer was dried with sodium sulfate and concentrated, and then the thus formed residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 550 mg (63%) of 3-(2,2-dimethyl-1,3-dioxan-4-yl)benzoic acid (Reference Example 15-1). FA: 237

Workup

additionwas added dropwise
additionAfter completion of the dropwise addition
customat −78° C.
customwas risen to room temperature
extractionextracted 10 times with chloroform-methanol (5:1)
dry with materialthe organic layer was dried with sodium sulfate
concentrationconcentrated
customthe thus formed residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-7625d93b79c44b4eb3594a7b2fdb7a12
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076367B2

Reaction notes

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