Carbon Dioxide → 2,3,4,5-Tetrahydro-1-benzoxepin-9-carboxylic acid

HRID 1723047Notes

Reaction equation

HRID 1723047 reaction equation
C([Li])CCC.CN(C)CCN(C)C.[O:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][CH2:16][CH2:15]1.[C:25](=[O:27])=[O:26]>CCCCCC.O>[O:14]1[C:20]2[C:21]([C:25]([OH:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 225522,3,4,5-Tetrahydro-1-benzoxepineHCID 178418339Butyllithium

Product 1

HCID 127011502,3,4,5-Tetrahydro-1-benzoxepin-9-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To 17.6 ml n-butyllithium (2.5M, 0.044 mol) in 63 ml hexane is added dropwise (0.044 mol) 5.1 g tetramethylethylenediamine (TMEDA) and 5 g (0.034 mol) of 2,3,4,5-tetrahydro-1-benzoxepin. The reaction mixture is stirred overnight. The reaction mixture is then chilled to 0° C. and carbonated with dry ice for an hour. Water (110 ml) is added and the mixture is filtered and the aqueous phase acidified with 4N HCl. The resultant oil is extracted into methylene chloride and dried (MgSO4). After filtering and concentrating in vacuo, 2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid results as a tan solid.

Workup

  1. filtrationthe mixture is filtered
  2. extractionThe resultant oil is extracted into methylene chloride
  3. dry with materialdried (MgSO4)
  4. filtrationAfter filtering
  5. concentrationconcentrating in vacuo, 2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid
  6. customresults as a tan solid

Sources & evidence

ORD record
ord-6fd8493b82e14b73b868158d7bc0ea19
Source dataset
uspto-grants-1989_08
Patent number
US04859683

Reaction notes

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