Sulfuric Acid → HCID 21458738, compound

HRID 264909Notes

Reaction equation

HRID 264909 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:15]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.S(=O)(=O)(O)O>O1CCCC1>[CH2:17]([O:16][C:8]1[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 54189192HCID 54189192, compound

Product 1

HCID 21458738HCID 21458738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.28 g of 5-benzyloxy-1,4-benzodioxane-7-carboxylic acid ethyl ester in 5 ml of tetrahydrofuran is added dropwise at room temperature to a solution of 110 mg of lithium aluminium hydride in 10 ml of tetrahydrofuran and the mixture is stirred at room temperature for a further 30 minutes. Then 0.22 ml of ethyl acetate, 1.5 ml of a mixture (water/tetrahydrofuran=1:1) and finally 2.25 ml of 2N sulfuric acid are added dropwise in succession. The reaction mixture is partitioned between diethyl ether and water. The organic phases are dried over sodium sulfate and concentrated by evaporation. The title compound is obtained from the residue by FC (240 g of silica gel, ethyl acetate/hexane=1:2): Rf (ethyl acetate-hexane=1:2)=0.18.

Workup

  1. customThe reaction mixture is partitioned between diethyl ether and water
  2. dry with materialThe organic phases are dried over sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-de84b72e86c04acebb9e90ef141843b2
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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