Sodium bis(trimethylsilyl)amide → HCID 18617849, compound

HRID 1264230Notes

Reaction equation

HRID 1264230 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[CH:23]=O)=[CH:18][CH:17]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCOCC>[CH3:25][C:22]([C:19]1[CH:20]=[CH:21][C:16]([C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)=[CH:17][CH:18]=1)([CH3:26])[CH:23]=[CH2:1]

Participants

6

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 18617539HCID 18617539, compound

Product 1

HCID 18617849HCID 18617849, compoundYield 111%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled slurry (0° C.) of methyltriphenylphosphonium bromide (18.8 g, 52.6 mmol) in THF (60 mL) is added dropwise (1M)sodium bis(trimethylsilyl)amide (52.6 mL, 52.6 mmol) and the resulting mixture stirred for 30 min. To the mixture is added a solution of 2-(4-furan-2-yl-phenyl)-2-methyl-propionaldehyde (5.64 g, 26.3 mmol) (reference example 52) in THF (25 mL) and the resulting mixture stirred for 45 min. The mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give 6.2 g of title compound as a yellow oil. 1H NMR (CDCl3) δ 1.41 (s, 6H), 5.03 (s, 1H), 5.08 (d, J=7 Hz, 1H), 6.03 (m, 1H), 6.45 (m, 1H), 6.60 (d, J=3 Hz, 1H), 7.36 (d, 8 Hz, 2H), 7.44 (s, 1H), 7.60 (d, J=8 Hz, 2H). MS (EI) m/z 212 (M+).

Workup

  1. stirringthe resulting mixture stirred for 45 min
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-580d286289804feeaba70870ff593232
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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