Tetrahydrofuran → HCID 14961821, compound

HRID 1681172Notes

Reaction equation

HRID 1681172 reaction equation
C1CO[C:3]2([C:6]([Sn:7]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])=[C:5]([CH3:20])[C:4]2=[O:21])[O:2]1.O1CCCC1.S(=O)(=O)(O)O.O>O>[CH3:20][C:5]1[C:4](=[O:21])[C:3](=[O:2])[C:6]=1[Sn:7]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14952258HCID 14952258, compoundHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 14961821HCID 14961821, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

2,2-Ethylenedioxy-4-methyl-3-(tri-n-butylstannyl)cyclobut-3-ene-1-one (450 mg) was added to a stirred mixture of tetrahydrofuran (4 mL) and sulfuric acid-H2O (3 mL of 1:1). The mixture was stirred at 22° C. for 2.5 hrs and then was diluted with H2O. The mixture was extracted with n-heptane (2X). The combined extracts were sequentially washed with H2O (2X) and saturated NaCl, dried (Na2SO4), and concentrated to leave the title compound (145 mg, 36% yield) as a yellow oil.

Workup

  1. extractionThe mixture was extracted with n-heptane (2X)
  2. washThe combined extracts were sequentially washed with H2O (2X) and saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-78c22f42d4994baa844daa1328c9d048
Source dataset
uspto-grants-1992_12
Patent number
US05169843

Reaction notes

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