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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
Notes
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Reaction equation

HRID 1003902 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dcea3567f7ed4aa781ae0c76789e4145
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06046355

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes