Oxalic Acid → 3-Pentyl-2-octenal

HRID 1110553노트

반응식

HRID 1110553 반응식
[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]

참가 물질

9

반응물 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 135616-UndecanoneHCID 178418339Butyllithium

생성물 1

HCID 145472433-Pentyl-2-octenal

시약·촉매·용매 4

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 13139Diethyl chlorophosphate용매HCID 138901N-Ethylidene-2-methylpropan-2-amine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a424265cb2b94496a5348fff39a8993f
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975438

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