Sodium bis(trimethylsilyl)amide → HCID 66577527, compound

HRID 73629Notes

Reaction equation

HRID 73629 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([CH:16]1[CH2:21][CH2:20][O:19][CH2:18][C:17]1=O)[CH2:12][CH2:13][CH:14]=[CH2:15]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:1]=[C:17]1[CH:16]([CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])[CH2:21][CH2:20][O:19][CH2:18]1

Participants

5

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 66577520HCID 66577520, compound

Product 1

HCID 66577527HCID 66577527, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

NaHMDS (5.35 ml, 10.70 mmol) was added to methyltriphenylphosphonium bromide (3822 mg, 10.70 mmol) in THF (53.500 ml) at RT. The reaction was stirred at RT for 1 hr before 4-(pent-4-en-1-yl)dihydro-2H-pyran-3(4H)-one (900 mg, 5.35 mmol) in THF (2 mL) was added at 0° C. The reaction mixture was stirred at room temperature for 2 hr. The mixture was cooled and quenched with aqueous NH4Cl. The reaction mixture was extracted with diethyl ether (3×20 mL). The combined organic fractions were washed with water and brine (saturated, 100 mL), dried, filtered and the solvent was evaporated under reduced pressure (400 mmhg). The residue was purified by column chromatography on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.75-5.89 (m, 1H), 4.92-5.06 (m, 2H), 4.86 (s, 1H), 4.77 (t, 1H, J=1.5 Hz), 4.12 (d, 1H, J=12.1 Hz), 3.86-3.96 (m, 2H), 3.57-3.65 (m, 1H), 2.15-2.24 (m, 1H), 2.00-2.12 (m, 2H), 1.81-1.91 (m, 1H), 1.64-1.76 (m, 1H), 1.21-1.52 (m, 4H).

Workup

  1. additionwas added at 0° C
  2. temperatureThe mixture was cooled
  3. customquenched with aqueous NH4Cl
  4. extractionThe reaction mixture was extracted with diethyl ether (3×20 mL)
  5. washThe combined organic fractions were washed with water and brine (saturated, 100 mL)
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure (400 mmhg)
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3a61578da656459f95ca2f5c5eb79c7e
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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