Carbon Dioxide → HCID 23661805, compound

HRID 1755925Notes

Reaction equation

HRID 1755925 reaction equation
C([Li:5])CCC.Br[C:7]1[CH:27]=[CH:26][C:10]2[O:11][C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][C:9]=2[CH:8]=1.[C:28](=[O:30])=[O:29]>O1CCCC1>[Li+:5].[C:14]1([C:12]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:11][C:10]3[CH:26]=[CH:27][C:7]([C:28]([O-:30])=[O:29])=[CH:8][C:9]=3[O:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 223195155-Bromo-2,2-diphenyl-1,3-benzodioxolHCID 178418339Butyllithium

Product 1

HCID 23661805HCID 23661805, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.25 ml of n-butyllithium (1.6M in n-hexane) in 50 ml of tetrahydrofuran is treated at -78° C. with 3.5 g of 5-bromo-2,2-diphenyl-1,3-benzodioxol and stirred for 10 minutes. The resulting solution is treated with about 10 g of solid carbon dioxide and subsequently warmed to room temperature. The precipitate formed is filtered off and dried. There are obtained 2.66 g of 2,2-diphenyl-1,3-benzodioxol-5-carboxylic acid lithium salt (1:1) as a white powder. This is dissolved in 20 ml of dimethylformamide and stirred at room temperature for 1 hour with 3.03 g of O-benzotriazol-1-yl-N,N,N',N'-tetra-methyluronium hexafluorophosphate (HBTU). The solvent is evaporated in a high vacuum, the residue is taken up in 15 ml of water and 15 ml of ethyl acetate and stirred in an ice bath for 45 minutes. The solid formed is filtered off under suction and dissolved in 40 ml of boiling ethyl acetate. A small amount of insoluble material is filtered off and the mother liquor is treated with n-hexane. The mixture is now concentrated until a suspension, which can still be filtered well, is obtained. The product is filtered off under suction and dried in a vacuum at 40° C. There are obtained 2.55 g of 1H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxol-5-carboxylate as white crystals of melting point 158°-160° C.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. customdried

Sources & evidence

ORD record
ord-1df731f1de5e457bbf38104a190a67c4
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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