tert-Butanol → HCID 86695136, compound

HRID 1503971Notes

Reaction equation

HRID 1503971 reaction equation
[CH2:1]([C:3]1(C(O)=O)[CH2:8][CH2:7][CH:6]([O:9][CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][CH2:4]1)[CH3:2].C1C=CC(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[C:39]([OH:42])(C)C>>[CH2:1]([C:3]1([N:35]=[C:39]=[O:42])[CH2:4][CH2:5][CH:6]([O:9][CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 68109704HCID 68109704, compound

Product 1

HCID 86695136HCID 86695136, compoundYield 73%

Procedure

A solution of 1-ethyl-4-[[2-(trimethylsilyl)ethoxy]methoxy]cyclohexane-1-carboxylic acid (1.24 g, 4.10 mmol, 1.00 equiv), DPPA (2.03 g, 7.38 mmol, 1.80 equiv) and TEA (1.24 g, 12.25 mmol, 2.99 equiv) in 2-methylpropan-2-ol (30 mL) was stirred for 14 hr at reflux under nitrogen. The reaction mixture was quenched with water, extracted with 3×50 mL of EtOAc. The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:6) to give (2-[[(4-ethyl-4-isocyanatocyclohexyl)oxy]methoxy]ethyl)trimethylsilane (0.9 g, 73%) as colorless oil. 1H NMR (400 MHz, CD3OD): δ 4.70 (2H, s), 3.89-3.80 (1H, m), 3.67 (2H, t), 1.80-1.73 (6H, m), 1.65-1.58 (4H, m), 1.00 (3H, t), 0.94 (2H, t).

Workup

  1. temperatureat reflux under nitrogen
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with 3×50 mL of EtOAc
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2f530382d6fc438ca29415c4520febeb
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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