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Ethanol → (5-tert-Butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenoxy)-acetic acid ethyl ester

HRID 1003902
ノート
印刷プレビュー

反応式

HRID 1003902 の反応式
[OH:1][C:2]1[CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[O:5][C:4](=[O:26])[CH:3]=1.[C:27]([C:31]1[C:32]([S:43]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:33][C:34]([CH3:42])=[C:35]([CH:41]=1)[O:36][CH2:37][C:38]([OH:40])=[O:39])([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:65][CH2:66]O>>[CH2:65]([O:40][C:38](=[O:39])[CH2:37][O:36][C:35]1[CH:41]=[C:31]([C:27]([CH3:28])([CH3:29])[CH3:30])[C:32]([S:43][C:3]2[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[CH2:7][C:2]=2[OH:1])=[CH:33][C:34]=1[CH3:42])[CH3:66]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 702EthanolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18798672[5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acidHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

生成物 1

HCID 70253780
(5-tert-Butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenoxy)-acetic acid ethyl ester

実験手順

The title compound was synthesized via General Method 9 using 209 mg (0.6 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 250 mg (0.6 mmol) of [5-tert-butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid (prepared in Example NNNN), 327 mg (2.4 mmol) of K2CO3, and DMF (2 mL). The reaction was conducted in EtOH to effect ester exchange. The reaction was worked up as described. The residue was chromatographed on silica gel eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH) to yield the product, m.p. 162-163° C. 1H NMR (DMSO-d6) δ 1.21 (t, 3 H), 1.47 (s, 9 H), 1.8 (s, 3 H), 2.0 (m, 4 H), 2.6 (m, 6 H), 2.95 (s, 2 H), 4.25 (q, 2 H), 4;75 (s, 2 H), 6.65 (m, 5 H), 6.75 (s, 1 H), 7.0 (d 4 H), 9.18 (s, 2 H).

後処理

  1. customThe residue was chromatographed on silica gel eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)
  2. customto yield the product, m.p. 162-163° C

出典と根拠

ORDレコード
ord-dcea3567f7ed4aa781ae0c76789e4145
出典データセット
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06046355

反応ノート

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