Triethylamine → HCID 19418512, compound

HRID 1648712Notes

Reaction equation

HRID 1648712 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-e6841d4c81ff4fc2aa77be8d4d6f83a1
Source dataset
uspto-grants-1995_07
Patent number
US05436359

Reaction notes

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