Potassium Carbonate → 3-(2-tert-Butyl-4-hydroxy-5-methylphenylsulfanyl)-6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

HRID 1003895노트

반응식

HRID 1003895 반응식
[CH:1]1([C:7]2([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[O:12][C:11](=[O:13])[CH:10]=[C:9]([OH:14])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([C:28]1[CH:33]=[C:32]([OH:34])[C:31]([CH3:35])=[CH:30][C:29]=1[S:36]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:24]([C:28]1[CH:33]=[C:32]([OH:34])[C:31]([CH3:35])=[CH:30][C:29]=1[S:36][C:10]1[C:11](=[O:13])[O:12][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:8][C:9]=1[OH:14])([CH3:27])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 10521842Toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) esterHCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

생성물 1

HCID 546822913-(2-tert-Butyl-4-hydroxy-5-methylphenylsulfanyl)-6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The title compound was prepared as described in General Method 9 from 6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example NN; 210 mg, 0.664 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) ester (prepared in Example RRR; 256 mg, 0.730 mmol), K2CO3 (367 mg, 2.655 mmol), and DMF (4 mL). The reaction was stirred at room temperature overnight and then worked up in the usual fashion. The crude product was flash chromatographed using CH2Cl2 :MeOH (98:2) to give the desired product as a solid, m.p. 100-103° C. 1H NMR (DMSO-6) δ 1.0-2.1 (m, 13 H), 1.45 (s, 9 H), 1.80 (s, 3 H), 2.5-2.6 (2 H +DMSO), 2.7 (d, 1 H), 2.9 (d, 1 H), 6.6-6.7 (d, s, 3 H), 6.77 (s, 1 H), 6.9 (d, 2 H), 9.01 (s, 1 H), 9.13 (s, 1 H).

후처리

  1. customThe title compound was prepared
  2. customchromatographed

출처 및 근거

ORD 기록
ord-7872fae7bcbf4083b39be31cd71fa2fd
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046355

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