Diethyl Ether → HCID 19432448, compound

HRID 654638Notes

Reaction equation

HRID 654638 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14][OH:15])=[CH:13][C:8]=3[O:7][C:6]=2[CH:16]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(N(CC)CC)C.C(OCC)C>C1COCC1.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14][O:15][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:13][C:8]=3[O:7][C:6]=2[CH:16]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 19432446HCID 19432446, compound

Product 1

HCID 19432448HCID 19432448, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-7-hydroxymethyl-dibenzofuran 9 (2.74 g, 9.9 mmol) and t-butyldimethylsilyl chloride (1.93 g, 12.8 mmol) in THF (60 ml) was added triethylamine (1.95 ml, 13.8 mmol) followed by 4-dimethylaminopyridine (120.7 mg, 0.99 mmol). After stirring at room temperature for 20 hours, the solution was poured into ethyl ether (180 ml) and washed successively with saturated NH4Cl, saturated NaHCO3, H2O, and brine. Drying (MgSO4) and evaporation gave a brown solid which was purified by flash chromatography through 100 g silica gel (10% CH2Cl2 -hexane) to yield 3.2 g (82%) of the title compound as a pale yellow solid.

Workup

  1. washwashed successively with saturated NH4Cl, saturated NaHCO3, H2O, and brine
  2. customDrying
  3. custom(MgSO4) and evaporation
  4. customgave a brown solid which
  5. customwas purified by flash chromatography through 100 g silica gel (10% CH2Cl2 -hexane)

Sources & evidence

ORD record
ord-6c5167dffb684859a119d728a7637e72
Source dataset
uspto-grants-1992_07
Patent number
US05132420

Reaction notes

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