Imidazole → HCID 131720964, compound

HRID 1456607Notes

Reaction equation

HRID 1456607 reaction equation
[OH:1][C:2]1[C:11]([C@H:12]([OH:17])[C@H:13]([CH3:16])[CH:14]=[CH2:15])=[C:10]2[C:5]([C:6]([CH2:19][CH2:20][CH3:21])=[CH:7][C:8](=[O:18])[O:9]2)=[C:4]([O:22][CH:23]([CH3:25])[CH3:24])[CH:3]=1.N1C=CN=C1.[C:31]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])([CH3:33])[CH3:32].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:1][C:2]1[C:11]([C@H:12]([O:17][Si:35]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:37])[CH3:36])[C@H:13]([CH3:16])[CH:14]=[CH2:15])=[C:10]2[C:5]([C:6]([CH2:19][CH2:20][CH3:21])=[CH:7][C:8](=[O:18])[O:9]2)=[C:4]([O:22][CH:23]([CH3:24])[CH3:25])[CH:3]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 88347803HCID 88347803, compound

Product 1

HCID 131720964HCID 131720964, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4a (500 mg, 1.44 mmol) in dry CH2Cl2 (20 mL) at 0° C. was added DMAP (88 mg, 0.72 mmol), imidazole (196 mg, 2.88 mmol) and tert-butylchlorodimethylsilane (239 mg, 1.59 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 24 h. Water (10 mL) was then added, the organic layer was separated, dried (MgSO4), concentrated and submitted to silica gel chromatography (Solvent B) to obtain 5a (583 mg, 88%) as a syrup: [α]D20 +38.0° (c 1.1, CHCl3); 1H NMR (CDCl3): δ -0.04 (s, 3 H, --SiCH3), 0.14 (s, 3 H, --SiCH3), 0.87 [s, 9 H, --C(CH3)3 ], 0.97 (d, 3 H, J=6.88 Hz, --CHCH3), 1.00 (t, 3 H, J=7.44 Hz, --CH2CH2CH3), 1.38 and 1.40 (2d, 6 H, J=6.0 Hz, --CH(CH3)2), 1.62 (m, 2 H, --CH2CH2CH3), 2.59 (q, 1 H, J=6.9 Hz, --CHCH3), 2.86 (bt, 2 H, --CH2CH2 CH3), 4.62 [m, 1 H, J=6.06 Hz, --CH(CH3)2 ], 4.95-5.05 (m, 2 H, --CH=CH2), 5.29 [d, 1 H, J=6.5 Hz, --CHOSi(CH3)2 --], 5.85 (m, 1 H, --CH=CH2), 5.89 (s, 1 H, H-3), 6.24 (s, 1 H, H-6), 9.15 (s, 1 H, ArOH); 13C NMR (CDCl3): δ -0.33, -0.15, 13.91, 16.27, 18.06, 21.76, 21.85, 23.08, 25.68, 25.88, 38.96, 44.62, 70.67, 74.28, 97.54, 103.39, 106.57, 109.86, 115.71, 139.60, 152.98, 156.13, 158.95, 160.17, 160.75. Anal. Calcd for C26H40 O5Si: C, 67.78; H, 8.75. Found C, 67.91; H, 8.71.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f3565da8b53f424fb5b0eb2669951955
Source dataset
uspto-grants-1998_12
Patent number
US05843990

Reaction notes

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