Methyl 4-iodosalicylate → Methyl 2-hydroxy-4-[3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate

HRID 22987노트

반응식

HRID 22987 반응식
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[C:7]([CH2:12][C:13]#[CH:14])[CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[OH:16][C:17]1[CH:26]=[C:25](I)[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I.C(N(CC)CC)C>[OH:16][C:17]1[CH:26]=[C:25]([C:14]#[C:13][CH2:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[O:5][CH2:4][CH2:3][C:2]3([CH3:15])[CH3:1])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

참가 물질

6

반응물 2

HCID 11380407Methyl 4-iodosalicylateHCID 225926343-(4,4-Dimethylchroman-8-yl)1-propyne

생성물 1

HCID 22592613Methyl 2-hydroxy-4-[3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8471Triethylamine용매

실험 절차

1.18 g (5.9 mmol) of 3-(4,4-dimethylchroman-8-yl)-1-propyne, 1.60 g (5.9 mmol) of methyl 2-hydroxy-4-iodobenzoate and 60 ml of triethylamine are introduced into a three-necked flask under argon. The reaction mixture is degassed by sparging with nitrogen, 332 mg (0.46 mmol) of bis(triphenylphosphine) palladium(II) chloride and 134 mg of copper iodide are introduced and the mixture is stirred at room temperature for eight hours. The reaction mixture is evaporated to dryness, the residue is taken up in ethyl acetate and hydrochloric acid (1N), and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a silica column eluted with heptane. After evaporating the solvents, an oil, which slowly crystallizes, is obtained and is recrystallized from heptane. 1.00 g (50%) of methyl 2-hydroxy-4-[3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate is collected in the form of a white solid with a melting point of 92-93° C.

후처리

  1. customThe reaction mixture is degassed
  2. additionare introduced
  3. customThe reaction mixture is evaporated to dryness
  4. customhydrochloric acid (1N), and the organic phase is separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue is purified by chromatography on a silica column
  8. washeluted with heptane
  9. customAfter evaporating the solvents
  10. customan oil, which slowly crystallizes
  11. customis obtained
  12. customis recrystallized from heptane
  13. custom1.00 g (50%) of methyl 2-hydroxy-4-[3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate is collected in the form of a white solid with a melting point of 92-93° C.

출처 및 근거

ORD 기록
ord-f82ec94a717e4aa488e5762c2b4726d9
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849658B2

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