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Phenylacetylene → Benzyl 2-benzyloxy-4-phenylethynyl-benzoate

HRID 322935
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HRID 322935 반응식
[CH2:1]([O:8][C:9]1[CH:24]=[C:23](I)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([C:32]#[CH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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.[Cu]Br.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([C:33]#[C:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 10821PhenylacetyleneHCID 10599389Benzyl 2-benzyloxy-4-iodobenzoate

생성물 1

HCID 10598112Benzyl 2-benzyloxy-4-phenylethynyl-benzoate수율 27.9%

시약·촉매·용매 3

HCID 24593copper(I) bromide촉매HCID 178418397HCID 178418397, 화합물촉매
HCID 8471
Triethylamine
용매

실험 절차

Benzyl 2-benzyloxy-4-iodobenzoate (7.6 g) is added to triethylamine (120 mL) followed by phenylacetylene (2.94 g) then tetrakis(triphenylphosphine)palladium(0) (0.664 g) and copper (I) bromide (0.248 g). The resulting mixture is stirred at room temperature for 3 hours. The triethylamine is distilled off and the residue partitioned between ether (600 mL) and saturated aqueous ammonium chloride solution. The organic phase is dried over magnesium sulphate and evaporated. The residue is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (5:1 v/v). Fractions homogeneous in the required product are combined and evaporated to give benzyl 2-benzyloxy-4-phenylethynyl-benzoate (2 g) as a cream solid, m.p. 98-100° C.

후처리

  1. distillationThe triethylamine is distilled off
  2. customthe residue partitioned between ether (600 mL) and saturated aqueous ammonium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. customThe residue is purified by flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (5:1 v/v)
  6. customevaporated

출처 및 근거

ORD 기록
ord-01ddd84156a7448b9f22bb951797c3bf
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211234B1

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