Stannane, [2,2'-bithiophen]-5-yltributyl- → 4-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene

HRID 1599512노트

반응식

HRID 1599512 반응식
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)CCC.[CH:24]([C:26]1[CH:30]=[C:29](I)[S:28][C:27]=1[CH2:32][OH:33])=[O:25]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O1CCCC1>[CH:24]([C:26]1[CH:30]=[C:29]([C:6]2[S:10][C:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][CH:7]=2)[S:28][C:27]=1[CH2:32][OH:33])=[O:25]

참가 물질

5

반응물 2

HCID 11201877Stannane, [2,2'-bithiophen]-5-yltributyl-HCID 189288892-(Hydroxymethyl)-5-iodothiophene-3-carbaldehyde

생성물 1

HCID 573213644-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene수율 38%

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

In a two-necked round bottomed flask was added 5-tributylstannyl-2,2'-bithiophene (2.04 g), bis(triphenylphosphine)palladium (II) chloride (0.19 g), 3-formyl-2-hydroxymethyl-5-iodo-thiophene (1.0 g) and tetrahydrofuran (20 ml). The reaction mixture was refluxed for 16 hours. Extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was separated by silica gel chromatography, eluted with n-hexane/ethyl acetate (9:1→1:1 gradient) to give brownish solid product (0.43 g, 38%), melting point 108°-110° C.

후처리

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. extractionExtracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was separated by silica gel chromatography
  7. washeluted with n-hexane/ethyl acetate (9:1→1:1 gradient)

출처 및 근거

ORD 기록
ord-39c20772fcec42f3b22ab542dcb257ec
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05741811

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