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Potassium Carbonate → 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 1003906
ノート
印刷プレビュー

反応式

HRID 1003906 の反応式
[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].C([O-])([O-])=O.[K+].[K+].NC1C=CC(CCC(=O)CCC2C=CC(N)=CC=2)=CC=1>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]
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 4

HCID 11430Potassium CarbonateHCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}esterHCID 540520781,5-Bis (4-amino-phenyl)-pentan-3-oneHCID 546822754-Hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

生成物 1

HCID 54682281
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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 K2CO3, and 10 mL of DMF. The reaction was worked up by addition of 10 mL 1. ON 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).

後処理

  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)

出典と根拠

ORDレコード
ord-d0be714c6e04473896454ca2adc775cd
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

読み込み中…

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