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Acetic Acid → Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonate

HRID 1902666
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인쇄 미리보기

반응식

HRID 1902666 반응식
C([Li])CCC.[CH3:6][O:7][P:8]([CH3:12])(=[O:11])[O:9][CH3:10].[CH3:13][CH:14]([CH2:16][C:17]#[C:18][CH2:19][CH3:20])[CH3:15].C(O)(=[O:23])C>CCCCCC.O1CCCC1>[CH3:6][O:7][P:8]([CH2:12][C:13](=[O:23])[CH:14]([CH3:15])[CH2:16][C:17]#[C:18][CH2:19][CH3:20])(=[O:11])[O:9][CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 1431226-Methyl-3-heptyneHCID 178418339Butyllithium

생성물 1

HCID 13269867Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 8058
Hexane
용매

실험 절차

646 ml of a 1.52% butyl lithium solution in hexane is dripped into a solution of 176 g of methane phosphonic acid dimethylester in 2 liters of tetra-hydrofuran at -70° C.; the mixture is stirred for 15 minutes and slowly a solution of 82.5 g of 2-methyl-hept-4-yne acid ethylester in 320 ml of tetrahydrofuran is added. This mixture is stirred for 4 h at -70° C., neutralized with acetic acid and vacuum evaporated. The residue is reacted with 200 ml of water, extracted three times with 600 ml of methylene chloride each time, the organic extract is shaken once with 100 ml of water, dried over magnesium sulfate and vacuum evaporated. The distillation of the residue in a 0.6 torr vacuum and at 120° C. yields 85 g of the title compound in the form of a colorless liquid.

후처리

  1. stirringThis mixture is stirred for 4 h at -70° C.
  2. customevaporated
  3. customThe residue is reacted with 200 ml of water
  4. extractionextracted three times with 600 ml of methylene chloride each time
  5. extractionthe organic extract
  6. stirringis shaken once with 100 ml of water
  7. dry with materialdried over magnesium sulfate and vacuum
  8. customevaporated
  9. distillationThe distillation of the residue in a 0.6 torr vacuum

출처 및 근거

ORD 기록
ord-fd8719da1d9e48beb35c4592ad10d64b
출처 데이터셋
uspto-grants-1982_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04364950

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