Didecylamine → N,N,N',N'-Tetradecyl-2-butene-1,4-diamine

HRID 275211노트

반응식

HRID 275211 반응식
[CH2:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(O[CH2:26][CH:27]=[CH:28][CH2:29]OC(=O)C)(=O)C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:12]([N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:26][CH:27]=[CH:28][CH2:29][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:29][CH2:28][CH2:27][CH3:26])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

5

반응물 2

HCID 14261DidecylamineHCID 1404022-Butene-1,4-diol diacetate

생성물 1

HCID 54366770N,N,N',N'-Tetradecyl-2-butene-1,4-diamine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of di-n-decylamine (10.9 g, 36.6 mmol) and 2-butene-1,4-diol diacetate (3.15 g, 18.3 mmol) in tetrahydrofuran (THF) (150 ml) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) and treated with 20% aqueous sodium hydroxide (250 ml). The mixture is stirred for one hour, concentrated, and extracted with ether. The ether extracts are dried and concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes). The title compound is isolated as 5.8 g (49% yield) of a clear oil.

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo to a oil that
  2. dissolutionis redissolved in THF (500 ml)
  3. additiontreated with 20% aqueous sodium hydroxide (250 ml)
  4. stirringThe mixture is stirred for one hour
  5. concentrationconcentrated
  6. extractionextracted with ether
  7. dry with materialThe ether extracts are dried
  8. concentrationconcentrated
  9. customgiving an orange oil which
  10. customis purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-094180197c384a0788740ca7dd012497
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391808

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