Diiodomethane → 4-(1-Methylcyclopropyl)phenol

Diethylzinc (1.0 M in hexanes, 69 mL, 69 mmol) was added to a solution of tert-butyl-(4-isopropenyl-phenoxy)-dimethyl-silane (6.85 g, 27.6 mmol) in dichloroethane at 0° C. Diiodomethane (11.2 mL, 138 mmol) was then added dropwise to the solution and the resultant mixture was stirred at 0° C. for 0.5 h and allowed to warm to rt for 2 h. The opaque mixture was quenched with saturated aqueous NH4Cl. The aqueous phase was extracted with CH2Cl2 and the combined organic layers were washed with saturated aqueous NaHCO3. The organic layers were dried over sodium sulfate, filtered through celite, and concentrated. The crude TBS ether was dissolved in THF (50 mL) and TBAF (1.0 M in THF, 28 mL, 28 mmol) was added at rt. The solution was stirred for 2 h and then quenched with aqueous 1.0 M HCl. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with saturated NaHCO3. The organic layers were dried over sodium sulfate, filtered and concentrated. Purification by silica-gel chromatography (1% 2-propanol/12% ethyl acetate in hexanes) provided 4-(1-methyl-cyclopropyl)-phenol (2.77 g, 68%) as a white solid.

1. customThe opaque mixture was quenched with saturated aqueous NH4Cl
2. extractionThe aqueous phase was extracted with CH2Cl2
3. washthe combined organic layers were washed with saturated aqueous NaHCO3
4. dry with materialThe organic layers were dried over sodium sulfate
5. filtrationfiltered through celite
6. concentrationconcentrated
7. dissolutionThe crude TBS ether was dissolved in THF (50 mL)
8. customquenched with aqueous 1.0 M HCl
9. extractionThe aqueous phase was extracted with ethyl acetate
10. washthe combined organic layers were washed with saturated NaHCO3
11. dry with materialThe organic layers were dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated
14. customPurification by silica-gel chromatography (1% 2-propanol/12% ethyl acetate in hexanes)

ORDレコード

ord-5c19c613203a404eabf271a87ab00192

出典データセット

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07569568B2