Tetrahydrofuran → HCID 21841002, compound

HRID 1739482Notes

Reaction equation

HRID 1739482 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH:16]1[O:20][CH2:19][CH2:18][O:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C([Li])CCC.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:11][C:10]=1[CH:16]1[O:20][CH2:19][CH2:18][O:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10928Ethyl chloroformateHCID 11244560HCID 11244560, compoundHCID 178418339Butyllithium

Product 1

HCID 21841002HCID 21841002, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of 2-(2-benzyloxy-5-bromophenyl)-1,3-dioxolane (7.8 g, 23.2 mmol) in freshly distilled THF (160 ml) was cooled to -75° C. with stirring under an argon atmosphere. To this solution was added n-butyl lithium (25.6 ml, 1.6 M in hexane) keeping the temperature below -70° C. The reaction mixture was stirred at -70° C. for 1 hour. The reaction was allowed to warm to -60° C. and added to a cooled (-60° C.) solution of ethyl chloroformate (5.05 g, 46.5 mmol) in freshly distilled THF (70 ml). The reaction was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was diluted with ethyl ether (100 ml), washed with ice/water (1×50 ml), saturated aqueous NaHCO3 (1×35 ml), brine (1×35 ml) dried over MgSO4 and evaporated. The product was purified by chromatography (eluant: ethyl ether/hexane) to give 2-(2-benzyloxy-5-ethoxycarbonylphenyl)-1,3-dioxolane as a colourless gum (4.2 g, 55%).

Workup

  1. customthe temperature below -70° C
  2. stirringThe reaction mixture was stirred at -70° C. for 1 hour
  3. additionadded to
  4. temperatureto warm to ambient temperature
  5. stirringstirred overnight
  6. washwashed with ice/water (1×50 ml), saturated aqueous NaHCO3 (1×35 ml), brine (1×35 ml)
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe product was purified by chromatography (eluant: ethyl ether/hexane)

Sources & evidence

ORD record
ord-1c9b97aebd414c07a096b378c935d0ee
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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