Oxalic Acid → 3-Pentyl-2-octenal

HRID 1110553Notes

Reaction equation

HRID 1110553 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(NC(C)C)(C)C.C([Li])CCC.[C:25](O)(=O)[C:26](O)=[O:27]>CCCCCC.C(N=CC)(C)(C)C.ClP(=O)(OCC)OCC.O1CCCC1>[CH2:5]([C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:25][CH:26]=[O:27])[CH2:4][CH2:3][CH2:2][CH3:1]

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 135616-UndecanoneHCID 178418339Butyllithium

Product 1

HCID 145472433-Pentyl-2-octenal

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 13139Diethyl chlorophosphateSolventHCID 138901N-Ethylidene-2-methylpropan-2-amineSolvent

Procedure

The compound was prepared according to the procedure described in Example 84 except that the reaction was worked up after 3 days. The following reagents were used: 6-undecanone (17 g). diisopropylamine (32.2 mL), 1.6M n-butyl lithium in hexane (143 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofuran (200 mL). The work up, varied only in that the oxalic acid catalyzed hydrolysis was run overnight at room temperature, gave the crude aldehyde which was purified by HPLC (ether-hexane; 1:16.6) to yield 15.5 g of 3-pentyl-2-octenal as an oil.

Workup

  1. customThe compound was prepared
  2. customhydrolysis
  3. waitwas run overnight at room temperature
  4. customgave the crude aldehyde which
  5. customwas purified by HPLC (ether-hexane; 1:16.6)

Sources & evidence

ORD record
ord-a424265cb2b94496a5348fff39a8993f
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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