Imidazole → HCID 57890161, compound

HRID 1819934Notes

Reaction equation

HRID 1819934 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([CH2:29][CH3:30])([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([OH:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([CH3:28])[CH:15]=2)[CH2:12][CH3:13])=[CH:8][C:9]=1[CH3:10])=[O:4].N1C=CN=C1.CN(C=O)C.[CH3:41][C:42]([Si:45](Cl)([CH3:47])[CH3:46])([CH3:44])[CH3:43]>CCOCC>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([O:27][Si:45]([C:42]([CH3:44])([CH3:43])[CH3:41])([CH3:47])[CH3:46])[C:23]([CH3:24])([CH3:25])[CH3:26])=[C:16]([CH3:28])[CH:15]=2)([CH2:12][CH3:13])[CH2:29][CH3:30])=[CH:8][C:9]=1[CH3:10])=[O:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 100714915-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 57890161HCID 57890161, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 5-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carboxylic acid methyl ester (Example 2) (1.15 g, 2.66 mmol), imidazole (0.27 g, 4.00 mmol), and DMF (15 mL) is added TBSCl (0.54 g, 2.80 mmol). The reaction is stirred for 24 h. The reaction is diluted with Et2O (120 mL) and washed with 0.1 M HCl (3×40 ml). The organic layer is MgSO4 dried and concentrated. The resulting residue is chromatographed to give the title compound (0.94 g, 64%). 1H NMR (CDCl3), δ 0.01 (s, 3H), 0.06 (s, 3H), 0.65 (t, J=7.4 Hz, 6H), 0.85 (s, 9H), 0.91 (s, 9H), 2.00-2.14 (m, 4H), 2.14 (s, 3H), 2.43 (s, 3H), 3.67 (dd, J=5.8, 3.4 Hz, 1H), 3.74 (s, 3H), 3.85 (dd, J=9.8, 5.8 Hz, 1H), 3.98 (dd, J=9.8, 3.4 Hz, 1H), 6.56 (s, 1H), 6.68 (d, J=8.3 Hz, 1H), 6.96-7.03 (m, 2H). LC/MS (m/z): calcd for C31H51O4SSi (M+H)+: 547.9; found: 547.2.

Workup

  1. washwashed with 0.1 M HCl (3×40 ml)
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting residue is chromatographed

Sources & evidence

ORD record
ord-87765967b66644f5b1ab3431e085a2ae
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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