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Dimethyl Sulfide → (R,E)-4-(2-naphtylthio)-3-buten-2-ol

HRID 1004496
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HRID 1004496 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]/[CH:12]=[CH:13]/[C:14](=[O:16])[CH3:15].C1(C2(C3C=CC=CC=3)OB(C)N3CCC[C@@H]23)C=CC=CC=1.CSC.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]/[CH:12]=[CH:13]/[C@H:14]([OH:16])[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1068Dimethyl SulfideHCID 25517Ammonium ChlorideHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 18795139(E)-4-(2-naphthylthio)-3-buten-2-one

생성물 1

HCID 15888161(R,E)-4-(2-naphtylthio)-3-buten-2-ol

시약·촉매·용매 1

HCID 1140
Toluene
용매
2회

실험 절차

(E)-4-(2-naphthylthio)-3-buten-2-one (228 mg, 1.0 mmol), (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2] oxazaborol (28 mg, 0.1 mmol) and MS4A (500 mg) were dried by a vacuum pump, followed by substituting with an argon gas. Dry toluene (5 ml) and dimethylsulfide (0.22 ml, 3.0 mmol) were added thereto and, after ice cooling, a solution of borane dimethylsulfide complex in toluene (1.07M, 0.65 ml, 0.7 mmol) was dropwise added. After stirring for two hours, an aqueous saturated ammonium chloride solution was added, followed by filtering through a cotton plug.

후처리

  1. filtrationby filtering through a cotton plug

출처 및 근거

ORD 기록
ord-31a9fc193d74402ebbf85a5650406951
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06049009

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