Phthalide → HCID 23672658, compound

HRID 1829066Notes

Reaction equation

HRID 1829066 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].[Li+:11].C[Si]([N-][Si](C)(C)C)(C)C.C1[CH2:25][O:24]CC1.C1C[O:29]CC1>>[O:2]=[C:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH:4]([C:25]([O-:24])=[O:29])[O:3]1.[Li+:11]

Participants

4

Reactant 3

HCID 6885PhthalideHCID 8028TetrahydrofuranHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23672658HCID 23672658, compoundYield 100%

Conditions

Temperature
-78 °C

Procedure

To a solution of phthalide (2.0 g, 14.9 mmol) in THF (60.0 ml) at −78° C. was added 1.0M LiHMDS/THF (15.7 ml) over 10 minutes. The reaction was stirred for 15 minutes at −78° C. and then the ice bath was removed. The reaction was quenched into dry ice using a cannula and then allowed to warm to room temperature. After adding 40 ml hexane, the cloudy mixture was rotary evaporated and chased with hexane to give lithium 3-oxo-1,3-dihydro-2-benzofuran-1-carboxylate as a yellow solid (2.86 g, 100%).

Workup

  1. customthe ice bath was removed
  2. customThe reaction was quenched into dry ice using a cannula
  3. temperatureto warm to room temperature
  4. additionAfter adding 40 ml hexane
  5. customthe cloudy mixture was rotary evaporated

Sources & evidence

ORD record
ord-ff966ed2050c4abd948034f90dc30c74
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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