Triethylamine → Ethyl 2-hydroxy-5-[[4-(4-methylphenoxysulfonyl)phenyl]ethynyl]benzoate

HRID 1653917

반응식

HRID 1653917 반응식
[OH:1][C:2]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1)#[CH:15].C(N(CC)CC)C.I.C(N(CC)CC)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:15]#[C:14][C:16]2[CH:17]=[CH:18][C:19]([S:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:23])=[O:24])=[CH:20][CH:21]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 10889681Triethylamine hydroiodideHCID 13013012Ethyl 2-hydroxy-5-iodobenzoateHCID 194234104-Methylphenyl 4-ethynylbenzenesulfonate

생성물 1

HCID 19423388Ethyl 2-hydroxy-5-[[4-(4-methylphenoxysulfonyl)phenyl]ethynyl]benzoate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Ethyl 2-hydroxy-5-iodobenzoate (58.5 g, 0.2 mol), 4-methylphenyl 4-ethynylbenzenesulfonate (54.4 g, 0.2 mol) and triethylamine (40 g, 0.4 mol) were dissolved in tetrahydrofuran (100 g). The solution was heated to 50° C. and dichlorobis(triphenylphosphine)palladium (0.5 g, 0.72 mmol) and copper(I)iodide (1 g, 5.2 mmol) were) added simultaneously with stirring. The reaction mixture turned dark and triethylamine hydroiodide started to precipitate after about 10 min. After keeping at 45° C. for 45 min, the suspension was poured into dilute hydrochloric acid and the mixture was extracted with toluene. The toluene solution was evaporated to dryness. The residue was triturated with acetonitrile, filtered off and dried. Yield 73 g, (84%). The pooled material from several batches (270 g) was recrystallized from acetonitrile (1.2 l). Yield 250 g.

후처리

  1. additionadded simultaneously
  2. customto precipitate after about 10 min
  3. additionthe suspension was poured into dilute hydrochloric acid
  4. extractionthe mixture was extracted with toluene
  5. customThe toluene solution was evaporated to dryness
  6. customThe residue was triturated with acetonitrile
  7. filtrationfiltered off
  8. customdried
  9. customThe pooled material from several batches (270 g) was recrystallized from acetonitrile (1.2 l)

출처 및 근거

ORD 기록
ord-27359a37178a4bbab4b2cf9f9c3d5332
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05403930

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