Diethyl Ether → HCID 19432448, compound

HRID 1886701Notes

Reaction equation

HRID 1886701 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-hydroxymethyldibenzofuran 3 (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-dfaceb2334ff449fbdfa417ee7607642
Source dataset
uspto-grants-1992_09
Patent number
US05151512

Reaction notes

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