Sodium bis(trimethylsilyl)amide → HCID 66579389, compound

HRID 73636Notes

Reaction equation

HRID 73636 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH:16]2[CH2:21][CH2:22][CH2:23][CH:24]=O)[O:14][CH2:13][CH2:12]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:21]([CH:16]1[CH2:17][O:18][CH2:19][CH2:20][C:15]21[O:11][CH2:12][CH2:13][O:14]2)[CH2:22][CH2:23][CH:24]=[CH2:1]

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 77231150HCID 77231150, compound

Product 1

HCID 66579389HCID 66579389, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a mixture of methyltriphenylphosphonium bromide (0.920 g, 2.58 mmol) in TI IF (10 mL) under N2 at it was added NaHMDS (2M in THF, 1.30 mL, 2.58 mmol). The mixture was stirred at rt for 1 hr. 4-(1,4,8-trioxaspiro[4.5]dec-6-yl)butanal (0.276 g, 1.29 mmol) was then added and the reaction was stirred at it for 1 hr. It was quenched with sat'd. aq. NH4Cl and extracted 3× with Et2O. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.75-5.86 (m, 1H), 4.91-5.03 (m, 2H), 3.91-4.05 (m, 4H), 3.78-3.90 (m, 2H), 3.62-3.71 (m, 1H), 3.43 (dd, 1H, J=9.0 Hz, 11.2 Hz), 1.98-2.12 (m, 2H), 1.11-1.81 (m, 7H).

Workup

  1. stirringthe reaction was stirred at it for 1 hr
  2. customIt was quenched with sat'd
  3. extractionaq. NH4Cl and extracted 3× with Et2O
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c12f529aa4524c07a053f8dda59feac5
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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