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Potassium Carbonate → 5-{[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl}-6-hydroxy-2-[2-(3-hydroxyphenyl)ethyl]-2-phenyl-2,3-dihydro-4h-pyran-4-one

HRID 1003915
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HRID 1003915 반응식
[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:23])[CH:3]=1.[C:24]([C:28]1[CH:33]=[C:32]([CH2:34][OH:35])[C:31]([CH3:36])=[CH:30][C:29]=1[S:37]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]([CH2:34][OH:35])[C:31]([CH3:36])=[CH:30][C:29]=1[S:37][C:3]1[C:4](=[O:23])[O:5][C:6]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][C:2]=1[OH:1])([CH3:27])([CH3:26])[CH3:25]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 54682293HCID 54682293, 화합물

생성물 1

HCID 546822925-{[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl}-6-hydroxy-2-[2-(3-hydroxyphenyl)ethyl]-2-phenyl-2,3-dihydro-4h-pyran-4-one

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

The title compound was prepared as described in General Method 9 using 4-hydroxy-6-[2-(3-hydroxy-phenyl)-ethyl]-6-phenyl-5,6-dihydro-pyran-2-one (0.155 g, 0.5 mmol) from Example UU, toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF; 0.2 g, 0.55 mmol), K2CO3 (0.27 g, 1.95 mmol), and DMF (3 mL). The solution was stirred overnight at room temperature, concentrated and the residue partitioned between 1N HCI and EtOAc. The organic phase was dried (MgSO4), and concentrated. Purification by silica gel chromatography, eluting with MeOH:CHCl3 :hexane (5:90:10 to 10:90:10) gave the title compound, m.p. 132-135° C. 1H NMR (DMSO-d6) δ 1.45 (s, 9 H), 1.76 (s, 3 H), 2.08-2.24 (m, 3 H), 2.48 (m, 1 H), 3.41 (dd, 2 H), 4.32 (s, 2 H), 4.91 (br s, 1 H), 6.17 (s, 1 H), 6.46-6.55 (m, 3 H), 7.02 (t, 1 H), 7.22 (s, 1 H), 7.35-7.46 (m, 5 H), 9.23 (s, 1 H), 12.15 (bs, 1 H).

후처리

  1. customThe title compound was prepared
  2. concentrationconcentrated
  3. customthe residue partitioned between 1N HCI and EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography
  7. washeluting with MeOH:CHCl3 :hexane (5:90:10 to 10:90:10)

출처 및 근거

ORD 기록
ord-3d2245e825014cd0a607f98ddb3349ac
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06046355

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