Ammonium Chloride → HCID 14758908, compound

HRID 1700952Notes

Reaction equation

HRID 1700952 reaction equation
C(C1C=CC(C2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.[Li].C([O:29][CH2:30][CH2:31][CH2:32][C@H:33]([CH3:43])[CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])C1C=CC=CC=1.[NH4+].[Cl-]>C1COCC1>[Si:36]([O:35][CH2:34][C@@H:33]([CH3:43])[CH2:32][CH2:31][CH2:30][OH:29])([C:39]([CH3:41])([CH3:42])[CH3:40])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 3028194LithiumHCID 11120848HCID 11120848, compound

Product 1

HCID 14758908HCID 14758908, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

With stirring, 4,4′-di-tert-butyl biphenyl (3.6 g) under an Argon atmosphere is added at 0° C. to a suspension of lithium (30% in mineral oil) in THF (30 ml). Stirring is continued for 2 h at r.t. The resulting deep green solution is added dropwise to a solution of (S)-1-benzyloxy-5-(ter-butyldimethylsilyloxy)-4-methyl-pentane 5 (673 mg, 2.09 mmol) in 10 ml of THF at −78° C., until the colour of the mixture remains green (or until tic analysis shows completion of the reaction, respectively). Saturated aqueous NH4Cl solution (10 ml) is added with stirring. The organic phase is separated and the aqueous layer is extracted with diethyl ether (3×50 ml). The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by flash column chromatography (pentane/diethyl ether 5:1) affords (S)-5-(tert-butyldimethylsilyloxy)-4-methyl-pentan-1-ol 6(471 mg, 97%) as a colourless oil. 13C-NMR (100 MHz, CDCl3): δ=68.29; 63.36; 35.57; 30.24; 29.25; 25.98; 18.38; 16.77; −5.34

Workup

  1. stirringStirring
  2. customcompletion of the reaction
  3. stirringwith stirring
  4. customThe organic phase is separated
  5. extractionthe aqueous layer is extracted with diethyl ether (3×50 ml)
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography (pentane/diethyl ether 5:1)

Sources & evidence

ORD record
ord-631364f9e1564c28bea786c033890abb
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

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