Diethyl Ether → [(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilane

HRID 1084321Notes

Reaction equation

HRID 1084321 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][OH:17])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C.C(OCC)C>C(Cl)Cl.C1COCC1.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 15159129(3-Bromophenanthren-9-YL)methanol2×

Product 1

HCID 15159130[(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilaneYield 87%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-9-(hydroxymethyl)phenanthrene, 4 (5.96 g, 20.8 mmol) and t-butyldimethylsilyl chloride (4.7 g, 31 mmol) in 100 ml of CH2Cl2 and 20 ml of THF was added triethylamine (4.9 ml, 35 mmol) followed by 4-dimethylaminopyridine (250 mg, 2.05 mmol). After stirring at room temperature for 20 hours, the solution was poured into 300 ml of ethyl ether and washed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine. Drying (Na2SO4) and evaporation gave a brown solid which was purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane) to yield 7.23 g (87%) of the title compound as a pale yellow solid.

Workup

  1. washwashed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine
  2. customDrying
  3. custom(Na2SO4) and evaporation
  4. customgave a brown solid which
  5. customwas purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane)

Sources & evidence

ORD record
ord-677571d4f10a4127b1531554855f793c
Source dataset
uspto-grants-1991_04
Patent number
US05004740

Reaction notes

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