Diethyl Ether → HCID 70155743, compound

HRID 1738085Notes

Reaction equation

HRID 1738085 reaction equation
[C:1]([C:4]1(C(O)=O)[CH:16]=[CH:15][C:14]2[N:13]([Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[C:12]3[CH2:11][CH2:10][CH:9]([N:27]([CH3:29])[CH3:28])[CH2:8][C:7]=3[C:6]=2[CH2:5]1)([OH:3])=O.[CH3:33][Li].C([O:37][CH2:38][CH3:39])C>O>[C:1]([C:4]1([C:38](=[O:37])[CH3:39])[CH:16]=[CH:15][C:14]2[N:13]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:24]([CH3:25])[CH3:26])[CH:18]([CH3:20])[CH3:19])[C:12]3[CH2:11][CH2:10][CH:9]([N:27]([CH3:29])[CH3:28])[CH2:8][C:7]=3[C:6]=2[CH2:5]1)(=[O:3])[CH3:33]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70156357HCID 70156357, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 70155743HCID 70155743, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.0 gm (4.8 mMol) 6-carboxy-3-(dimethyl)amino-6-carboxy-9-triisopropylsilyl-1,2,3,4-tetrahydro-9H-carbazole in 100 mL diethyl ether at 0° C. were added 8 mL (9.6 mMol) methyllithium (1.2 M in diethyl ether) over a 15 minute period. After an hour an additional 0.4 mL of the methyllithium solution were added. 0.4 mL additions were continued until all of the starting material had reacted. The reaction mixture was then allowed to warm to room temperature and to it was first added ice and then the reaction mixture was diluted with 100 mL of water. The mixture was shaken and the phases separated. The aqueous phase was twice extracted with 100 mL aliquots of fresh diethyl ether. All of the organic extracts were combined, washed with saturated aqueous sodium chloride and concentrated under reduced pressure. The residue was subjected to florisil chromatography, eluting sequentially with toluene, 9:1 toluene:ethyl acetate, 4:1 toluene:ethyl acetate, 1:1 toluene:ethyl acetate, and ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to give 1.37 gm (69%) of the desired product as a solid.

Workup

  1. customhad reacted
  2. customthe phases separated
  3. extractionThe aqueous phase was twice extracted with 100 mL aliquots of fresh diethyl ether
  4. washwashed with saturated aqueous sodium chloride
  5. concentrationconcentrated under reduced pressure
  6. washeluting sequentially with toluene, 9:1 toluene
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-973bfbc278aa4a958aa22dafe929b4a6
Source dataset
uspto-grants-1999_10
Patent number
US05962473

Reaction notes

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