Triethylamine → HCID 54416712, compound

HRID 370318Notes

Reaction equation

HRID 370318 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].[Br-].[Mg+2].[Br-].C(N(CC)CC)C.[CH3:26][S:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1>C1COCC1.O.CCCCCC>[CH3:7][C:6](=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([S:27][CH3:26])=[CH:29][CH:30]=1)[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 769854-(Methylthio)benzaldehydeHCID 82241Magnesium BromideHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 54416712HCID 54416712, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of triethyl 2-phosphonopropionate (47 g, 0.19 mol) in THF (200 mL) was added solid magnesium bromide etherate (59 g, 0.23 mol) under nitrogen. Triethylamine (26.5 mL, 0.19 mol) was added after 5 min. The mixture was stirred for 10 min and 4-(methylthio)benzaldehyde (27.1 mL, 0.19 mol) was added. After 15 h at room temperature the mixture was diluted with water (400 mL) and hexane (400 mL). The two layers were separated. The organic layer was washed with water (400 mL), dried over 4 Å molecular sieves, filtered, and concentrated to give 42.5 g (95%) of ester 6a as a light yellow oil: IR (neat) 2980, 1705, and 1240 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 7.63 (1 H), 7.33 (2 H), 7.25 (2 H), 4.26 (2 H), 2.50 (3 H), 2.12 (3 H), and 1.34 (3 H); 13C NMR (CDCl3, 75.5 MHz) δ 168.71, 139.37, 138.08, 132.55, 130.19, 127.98, 125.89, 60.87, 15.38, 14.37 and 14.17.

Workup

  1. customThe two layers were separated
  2. washThe organic layer was washed with water (400 mL)
  3. customdried over 4 Å molecular sieves
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-11c045263ed64978a107e051f15eea11
Source dataset
uspto-grants-2000_10
Patent number
US06140515

Reaction notes

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