Imidazole → HCID 59864416, compound

HRID 1093937Notes

Reaction equation

HRID 1093937 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]2[C:3]=1[C:4]1[CH2:21][CH2:20][CH2:19][CH2:18][C:5]=1[C:6](=[O:17])[O:7]2.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28].CCOCC>CN(C=O)C>[Si:31]([O:1][C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[C:8]2[C:3]=1[C:4]1[CH2:21][CH2:20][CH2:19][CH2:18][C:5]=1[C:6](=[O:17])[O:7]2)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 59864392HCID 59864392, compound

Product 1

HCID 59864416HCID 59864416, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

32 g (112 mmol) of 1-hydroxy-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one were initially introduced in 200 ml of DMF, 10 g of imidazole (145 mmol) were added, a solution of 21 g (135 mmol) of tert-butyldimethyl-silyl chloride in 100 ml of DMF was added dropwise at 0° C., and the mixture was stirred at room temp. for 20 h. MTB ether was subsequently added to the batch, which was then washed with water and dried over sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography with heptane/ethyl acetate (6:1), giving 44.5 g (94%) of 1-tert-butyl-dimethylsilyloxy-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one as a yellow solid.

Workup

  1. washwas then washed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by chromatography with heptane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-c5a36afb56f4464280202829c0d486a7
Source dataset
uspto-grants-2012_03
Patent number
US08133887B2

Reaction notes

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