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Hydrochloric Acid → 5-[2-tert-butyl-4-(2-hydroxyethoxy)-5-methyl-phenyl]sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxy-3-methoxy-phenyl)ethyl]-3H-pyran-6-one

HRID 356552
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HRID 356552 반응식
[OH:1][C:2]1[CH2:7][C:6]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=2)[O:5][C:4](=[O:30])[CH:3]=1.[C:31]([C:35]1[CH:40]=[C:39]([O:41][CH2:42][CH2:43][O:44][Si](C(C)(C)C)(C)C)[C:38]([CH3:52])=[CH:37][C:36]=1[S:53]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:34])([CH3:33])[CH3:32].Cl>CN(C=O)C>[C:31]([C:35]1[CH:40]=[C:39]([O:41][CH2:42][CH2:43][OH:44])[C:38]([CH3:52])=[CH:37][C:36]=1[S:53][C:3]1[C:4](=[O:30])[O:5][C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=2)([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=2)[CH2:7][C:2]=1[OH:1])([CH3:34])([CH3:33])[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}esterHCID 546822754-Hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

생성물 1

HCID 546822815-[2-tert-butyl-4-(2-hydroxyethoxy)-5-methyl-phenyl]sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxy-3-methoxy-phenyl)ethyl]-3H-pyran-6-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The compound was prepared using General Method 9 and the following quantities: 100 mg (0.24 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example QQ), 123 mg (0.24 mol) of toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl} ester (prepared in Example PPP), 133 mg (0.96 mmol) of K2 CO3, and 10 mL of DMF. The reaction was worked up by addition of 10 mL 1.0N HCl and stirring for 10 minutes, followed by extraction with EtOAc. The organic layer was dried (Na2SO4), concentrated, and chromatographed on silica gel, eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH), to give the title compound, m.p. 76°-82° C. 1H NMR (DMSO-d6) δ 1.5 (s, 9 H), 1.75 (s, 3 H), 2.05 (m, 4 H), 2.6 (m, 4 H), 2.95 (s, 2 H), 3.7 (m, 8 H), 3.95 (t, 2 H), 4.8 (br s, 1 H), 6.65 (m, 7 H), 7.0 (s, 1 H), 8.75 (s, 2 H).

후처리

  1. customThe compound was prepared
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. washeluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)

출처 및 근거

ORD 기록
ord-46f03ad042af43be9c5f82644cf0e21a
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05834506

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