4-tert-Butyldimethylsilyloxybenzeneacetic Acid Methyl Ester → 2-(4-((Tert-butyldimethylsilyl)oxy)phenyl)ethan-1-ol

HRID 1878758Notes

Reaction equation

HRID 1878758 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](OC)=[O:23])=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>C(OCC)C>[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 137534164-tert-Butyldimethylsilyloxybenzeneacetic Acid Methyl EsterHCID 21226445Aluminium lithium hydride

Product 1

HCID 112882212-(4-((Tert-butyldimethylsilyl)oxy)phenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring suspension of lithium aluminum hydride (893 mg, 23.5 mmol) in diethyl ether (30 mL) at 0° C. under nitrogen was added dropwise a solution of methyl 2-(4-(tert-butyldimethylsilyloxy)phenyl)acetate (3300 mg, 11767 μmol) in diethyl ether (20 mL). The mixture was stirred for 90 min, then quenched with solid sodium sulfate hexahydrate (10 g). The suspension was stirred for 45 min and the salts were removed via filtration with ether washings. The solvents were removed under reduced pressure and the residue was purified on 120 grams of silica eluting with 0-20% EtOAc/hexane to give a colorless oil. MS (ESI pos. ion) m/z (MH+): 255. Calc'd exact mass for C14H24O2Si: 254. 1H NMR (400 MHz, Chloroform-d) δ ppm 0.19 (s, 6 H) 0.98 (s, 9 H) 1.39 (t, J=6.02 Hz, 1 H) 2.80 (t, J=6.53 Hz, 2 H) 3.82 (q, J=6.19 Hz, 2 H) 6.78 (d, J=8.53 Hz, 2 H) 7.08 (d, J=8.53 Hz, 2 H).

Workup

  1. customquenched with solid sodium sulfate hexahydrate (10 g)
  2. stirringThe suspension was stirred for 45 min
  3. customthe salts were removed via filtration with ether washings
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was purified on 120 grams of silica eluting with 0-20% EtOAc/hexane
  6. customto give a colorless oil

Sources & evidence

ORD record
ord-d60e4e42e6bf4adb8fbbb1b44ba4ee2a
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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