Triethylamine → HCID 11644309, compound

HRID 1796872Notes

Reaction equation

HRID 1796872 reaction equation
[CH:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(C(CC)(OP([CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])(O)=O)C)C.[Br-].[Li+].C(N(CC)CC)C>C1COCC1>[CH:1]1(/[CH:6]=[CH:16]/[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70106CyclopentanecarbaldehydeHCID 82050Lithium BromideHCID 91327948HCID 91327948, compound

Product 1

HCID 11644309HCID 11644309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopentanecaboxaldehyde (0.069 g, 0.70 mmol), benzyl (diethylethyl phosphono)acetate (0.100 g, 0.35 mmol), lithium bromide (0.030 g, 0.35 mmol), and triethylamine (0.049 mL, 0.35 mmol) in THF (1 mL) at room temperature was stirred for 16 hours, quenched with water, stirred for 15 minutes, diluted with ethyl acetate, washed sequentially with pH 7 buffer and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 231 (M+H)+.

Workup

  1. customquenched with water
  2. additiondiluted with ethyl acetate
  3. washwashed sequentially with pH 7 buffer
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1967cf2cdefe4012ac77faad212502f6
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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