Triethylamine → HCID 19418512, compound

HRID 864708Notes

Reaction equation

HRID 864708 reaction equation
[Si]([O:18][C:19]1[C:24]([CH3:25])=[C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)C(O)=[C:21]([O:57][CH3:58])[C:20]=1[O:59][CH3:60])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[C:61]([O:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])(OC(C)(C)C)=O.C(N(CC)CC)C>ClCCl>[C:72]([O:71][C:69]([O:68][C:61]1[C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[C:24]([CH3:25])[C:19]([OH:18])=[C:20]([O:59][CH3:60])[C:21]=1[O:57][CH3:58])=[O:70])([CH3:73])([CH3:74])[CH3:75]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 15294995HCID 15294995, compound

Product 1

HCID 19418512HCID 19418512, compoundYield 150.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-tert-butyldiphenylsilyloxy-2,3-dimethoxy-5-methyl-6-(10-trityloxydecyl)phenol (8 g), di-tert-butyl dicarbonate (3 g), triethylamine (1 g) and dichloromethane (20 ml) was stirred at 40° C. for 16 hours. After concentration under reduced pressure, the residue was dissolved in tetrahydrofuran (30 ml). Tetrabutylammonium fluoride trihydrate (2 g) was added, and the mixture was stirred at room temperature for 15 minutes. The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography on silica gel and eluted with hexane/ethyl acetate (7:3) to obtain the desired compound (10 g).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in tetrahydrofuran (30 ml)
  3. additionTetrabutylammonium fluoride trihydrate (2 g) was added
  4. stirringthe mixture was stirred at room temperature for 15 minutes
  5. distillationThe solvent was distilled off under reduced pressure
  6. washeluted with hexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-c2c37339b234483d9d4e50ef500071a4
Source dataset
uspto-grants-1996_10
Patent number
US05563129

Reaction notes

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