Dimethylformamide → 3-[2-tert-Butyl-4-(2-hydroxy-ethoxy)-5-methyl-phenylsulfanyl]-4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 356547노트

반응식

HRID 356547 반응식
[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[CH:36]=[C:35]([O:37][CH2:38][CH2:39][O:40][Si](C(C)(C)C)(C)C)[C:34]([CH3:48])=[CH:33][C:32]=1[S:49]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CO.Cl>[C:27]([C:31]1[CH:36]=[C:35]([O:37][CH2:38][CH2:39][OH:40])[C:34]([CH3:48])=[CH:33][C:32]=1[S:49][C:3]1[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[CH2:7][C:2]=1[OH:1])([CH3:30])([CH3:29])[CH3:28]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}esterHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

생성물 1

HCID 546822993-[2-tert-Butyl-4-(2-hydroxy-ethoxy)-5-methyl-phenylsulfanyl]-4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

The title compound was synthesized using General Method 9 using 0.07 g (2 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 1.00 g (2 mmol) of toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl} ester (prepared in Example PPP), 1.06 g (8 mmol) K2CO3, and DMF (5 mL). The solid which was obtained was then dissolved in 20 mL MeOH and 2 mL of 1N HCl. After 15 minutes the reaction was concentrated and the residue partitioned between EtOAc and H2O; the organic layer was separated, dried (Na2SO4) and concentrated. Trituration with Et2O yielded the title compound, m.p. 106°-107° C. 1H NMR (DMSO-d6) δ 1.49 (s, 9 H), 1.75 (s, 3 H), 2.0 (t, 4 H), 2.5 (t, 4 H), 3.4 (dd, 2 H), 3.7 (bs, 2 H), 3.95 (t, 2 H), 4.8 (br s, 1 H), 6.66 (d, 4 H), 6.7 (s, 1 H), 6.8 (s, 1 H), 6.98 (d, 4 H), 9.17 (s, 2 H).

후처리

  1. customThe title compound was synthesized
  2. customThe solid which was obtained
  3. concentrationAfter 15 minutes the reaction was concentrated
  4. customthe residue partitioned between EtOAc and H2O
  5. customthe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-602010b937804b82ae923dd39b34c0a9
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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