반응식
C(OC1C(OC)=CC(Cl)=CC=1CC(O)CO)C1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([O:44][CH2:45][CH:46]([OH:65])[CH2:47][C:48]2[CH:53]=[C:52]([Cl:54])[CH:51]=[C:50]([O:55][CH3:56])[C:49]=2[O:57]CC2C=CC=CC=2)(=[O:43])=[O:42])=[CH:37][CH:36]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.Cl>N1C=CC=CC=1.[Pd]>[CH3:34][C:35]1[CH:36]=[CH:37][C:38]([S:41]([O:44][CH2:45][CH:46]([OH:65])[CH2:47][C:48]2[CH:53]=[C:52]([Cl:54])[CH:51]=[C:50]([O:55][CH3:56])[C:49]=2[OH:57])(=[O:43])=[O:42])=[CH:39][CH:40]=1참가 물질
반응물 5
생성물 1
시약·촉매·용매 2
실험 절차
Treatment of (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]propane-1,2-diol (32.28 g, 0.1 mol) with p-toluenesulfonyl chloride (21 g, 0.11 mol) in pyridine (1000 mL) generally according to the procedure described for Intermediate 18 provided (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the tosylate with palladium on carbon (5 wt. %, 2.32 g) and hydrogen chloride (19 mL, 4.0 M in isopropanol) generally according to the procedure described for Intermediate 4 gave (±)-3-(5-chloro-2-hydroxy-3-methoxyphenyl)-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the phenyl with triphenylphosphine (23.6 g, 0.09 mol) and diisopropyl azodicarboxylate (18.2 g, 0.09 mol) generally according to the procedure described for Intermediate 5 gave 28.2 g (76%) of (±)-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a pale yellow solid. mp 99-102° C.; Anal. calcd. for C17H17ClO5S: C, 55.36; H, 4.65. Found: C, 55.35; H, 4.62.
출처 및 근거
- ORD 기록
- ord-cdf570fc775b4f2c9c57bd8de576ce98
- 출처 데이터셋
- uspto-grants-2010_06
- 특허 번호
- US07728155B2
연결된 노트
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