Triethylamine → 3-(3'-Tert-butyldimethylsilyloxy-4'-methoxyphenyl)-6-methoxybenzo[b]furan

HRID 9306Notes

Reaction equation

HRID 9306 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=3[O:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CCN(CC)CC.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:32]([O:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=3[O:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 219865573-(3'-Hydroxy-4'-methoxyphenyl)-6-methoxybenzo[b]furan

Product 1

HCID 219865593-(3'-Tert-butyldimethylsilyloxy-4'-methoxyphenyl)-6-methoxybenzo[b]furanYield 92.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 14 (3.51 g, 12.9 mmol) in CH2Cl2 (30 mL), under nitrogen, was added Et3N (1.98 mL, 14.2 mmol) followed by DMAP (0.162 g, 14.2 mmol) and TBSCl (2.4 g, 14.2 mmol) at 0° C. The reaction mixture was stirred for 12 h allowing too reach room temperature. The reaction was quenched with water, the phases separated, and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexanes) afforded 4.57 g (11.9 mmol, 92%) of the protected benzo[b]furan 15 as a colorless oil.

Workup

  1. customallowing too reach room temperature
  2. customThe reaction was quenched with water
  3. customthe phases separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. washby flash column chromatography (silica gel, elution with hexanes)

Sources & evidence

ORD record
ord-d172a1b84e4647bc9c8687f1cd8f5dda
Source dataset
uspto-grants-2006_08
Patent number
US07091240B2

Reaction notes

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