HCID 58672952, compound → HCID 58672950, compound

HRID 749627Notes

Reaction equation

HRID 749627 reaction equation
[CH2:1]([Li])CCC.[Si:6]([O:13][C@@H:14]1[CH2:19][CH:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][C@@H:16]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C:15]1=O)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:21]([O:20][CH:18]1[CH2:17][C@@H:16]([O:28][Si:29]([C:32]([CH3:35])([CH3:33])[CH3:34])([CH3:30])[CH3:31])[C:15](=[CH2:1])[C@H:14]([O:13][Si:6]([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:8])[CH3:7])[CH2:19]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 58672952HCID 58672952, compoundHCID 178418339Butyllithium

Product 1

HCID 58672950HCID 58672950, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of methyltriphenylphosphonium bromide (1.55 g, 4.34 mmol) in dry THF (10 mL) cooled to 0° C. was added n-butyl lithium (n-BuLi, 2.71 mL, 4.34 mmol, 1.6 M solution in hexane), and the mixture was stirred for 10 min, and further stirred for 1 h at room temperature. To the resulting orange mixture was added over ca. 20 min period a solution of Compound 6 (1.0 g, 2.15 mmol) dissolved in dry THF (10 mL). After being stirred for 1 h at 0° C. and for 17 h at room temperature, the reaction mixture was poured into ice water, and extracted with AcOEt. The organic layer was rinsed with saturated brine, and dried over anhydrous MgSO4. The solvent was removed by evaporation. The residue was purified by silica gel column chromatography (5 g; 2% AcOEt/hexane), to yield Compound 7 (978.5 mg, 98%, single compound).

Workup

  1. stirringfurther stirred for 1 h at room temperature
  2. stirringAfter being stirred for 1 h at 0° C. and for 17 h at room temperature
  3. extractionextracted with AcOEt
  4. washThe organic layer was rinsed with saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was removed by evaporation
  7. customThe residue was purified by silica gel column chromatography (5 g; 2% AcOEt/hexane)

Sources & evidence

ORD record
ord-d0dc37de450b4a17949496402ede21d5
Source dataset
uspto-grants-2008_07
Patent number
US07402688B2

Reaction notes

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