3,3-Dimethyl-1-butanol → HCID 59949582, compound

HRID 1532875Notes

Reaction equation

HRID 1532875 reaction equation
[CH:1]1([CH2:7][C@H:8]2[CH2:10][O:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][OH:15]>CN(C=O)C.[H-].[Na+]>[CH:1]1([CH2:7][C@H:8]([OH:9])[CH2:10][O:15][CH2:14][CH2:13][C:12]([CH3:17])([CH3:16])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 122333,3-Dimethyl-1-butanolHCID 59949024HCID 59949024, compound

Product 1

HCID 59949582HCID 59949582, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 24758Sodium hydrideSolvent

Procedure

The product from Example 1308C (435 mg, 3.1 mmol) in DMF (2.0 mL), 3,3-dimethylbutanol (400 μL, 3.3 mmol) in DMF (3.0 mL) and NaH, 60% dispersion in mineral oil, (145 mg, 3.6 mmol) in DMF (7.0 mL) were allowed to react in a manner similar to that described in Example 1308D. The residue was chromatographed (silica gel; EtOAc/hexanes, 1:20) to afford a light yellow oil (458 mg, 57%). 1H NMR (CDCl13, 300 MHz) δ0.78-1.01 (m, 2H), 0.92 (s, 9H), 1.11-1.57 (m, 8H), 1.62-1.85 (m, 5H), 3.21 (dd, J=8, 9 Hz, 1H), 3.40-3.66 (m, 3H), 3.89 (m, 1H); MS (CI/NH3) m/z: (M+NH4)+ 260.

Workup

  1. customto react in a manner similar to
  2. customThe residue was chromatographed (silica gel; EtOAc/hexanes, 1:20)

Sources & evidence

ORD record
ord-e3c34f76db0a42249ecbade7e52ae854
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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