Imidazole → HCID 54157985, compound

HRID 258159Notes

Reaction equation

HRID 258159 reaction equation
[OH:1][CH2:2][C:3]1([CH2:8][C@@H:9]([OH:20])[C@H:10]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:11]=[CH2:12])[O:7][CH2:6][CH2:5][O:4]1.N1C=CN=C1.[CH3:26][C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(=O)(O)[O-].[Na+]>ClCCl>[Si:30]([O:1][CH2:2][C:3]1([CH2:8][C@@H:9]([OH:20])[C@H:10]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:11]=[CH2:12])[O:4][CH2:5][CH2:6][O:7]1)([C:27]([CH3:29])([CH3:28])[CH3:26])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 67872302HCID 67872302, compound

Product 1

HCID 54157985HCID 54157985, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Compound 10 (6.55 g, 22.4 mmol) in dichloromethane (40 mL) at zero degrees C was treated with imidazole (3.21 g, 47.2 mmol), and then TBSCl (3.47 g, 23.1 mmol) in dichloromethane (20 mL) and stirred for two hours. The mixture was poured into saturated aqueous sodium bicarbonate solution (100 mL), extracted with dichloromethane (3×50 mL), concentrated, and the residue purified by flash chromatography (ether) to give Compound 10-1 (8.88 g, 98 percent) as a colorless oil; Rf =0.51 (Et2O); [a]D25 =-33.3° (c 5.3, CH2Cl2); IR (thin film) νmax 3490 cm-1 ; 1H NMR (500 MHz, CDCl3) δ 5.77 (m, 1 H, CH=CH2), 5.30-5.26 (m, 2 H, CH=CH2), 4.73 (ABq, J =6.5 Hz, Dn =40 Hz, 2 H, OCH2O), 4.03-3.95 (m, 5 H, CH--OH, ethylene ketal), 3.93 (dd, J =5.4, 10.0 Hz, 1 H, CH--OMEM), 3.82 (m, 1 H, OCHH--CH2 --OMe), 3.61 (m, 1 H, OCHH--CH2 --OMe), 3.55 (ABq, J =10.4 Hz, Dn =23 Hz, 2 H, CH2 --OTBS), 3.53 (m, 2 H, OCH2CH2 -13 OMe), 3.48 (bs, 1 H, OH), 3.37 (s, 3 H, OMe), 1.94 (dd, J =1.4, 14.9 Hz, 1 H, CHH), 1.83 (dd, J =10.0, 14.9 Hz, 1 H, CHH), 0.88 (s, 9 H, tBu), 0.04 (s, 6 H, SiMe2); 13C NMR (125 MHz, CDCl3) δ 134.7, 119.3, 110.4, 92.9, 80.2, 71.7, 69.5, 67.0, 66.2, 65.5, 65.1, 65.1, 58.9, 37.2, 25.8, 18.2, -5.5; FAB HRMS (NBA/CsI) m/e 539.1430, M+Cs+ calcd for C19H38O7Si 539.1441.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. concentrationconcentrated
  3. customthe residue purified by flash chromatography (ether)

Sources & evidence

ORD record
ord-56351649043749f3926fd11ad9a8c7e3
Source dataset
uspto-grants-1993_11
Patent number
US05264586

Reaction notes

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