Water → HCID 68408341, compound

HRID 1176164Notes

Reaction equation

HRID 1176164 reaction equation
[CH2:1](OC1C=CC(C#C[Si](C)(C)C)=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-:26].[Na+].O.[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>CO>[CH2:12]([O:26][C:31]#[C:30][C:29]1[CH:33]=[CH:4][CH:3]=[CH:2][CH:1]=1)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68408307HCID 68408307, compound

Product 1

HCID 68408341HCID 68408341, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Dodecyloxy[(trimethylsilyl)ethynyl]benzene (3.09 g, 8.62×10−3 mol) was dissolved in a mixture of 20 ml of MeOH and 20 ml of THF. 5N NaOH (2.1 ml, 1.05×10−2 mol) was added and the solution was stirred for 3.5 h at room temperature under N2. Water was added to the reaction mixture. The aqueous layer was extracted three times with CH2Cl2. The combined organic layers were dried over MgSO4. The product was chromatographed on silica gel with 4:1 hexane:CH2Cl2 as the eluent. Yield=2.430 g (98% based on 3.09 g of 4-dodecyloxy[(trimethylsilyl)ethynyl]benzene). 1H NMR (250 MHz, CDCl3): δ 7.41 (d, 2H, J=8.8 Hz, Ph), 6.83 (d, 2H, J=8.7 Hz, Ph), 3.95 (t, 2H, J=6.6 Hz, —OCH2—), 2.99 (s, 1H, ethynyl-H), 1.78 (quint, 2H, J=6.9 Hz, —OCH2CH2—), 1.10-1.51 (m, 18H, —CH2—), 0.88 (t, 3H, J=6.6 Hz, —CH3). CI MS m/z: 287.236 ((M+H)+) (calcd 287.237).

Workup

  1. extractionThe aqueous layer was extracted three times with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customThe product was chromatographed on silica gel with 4:1 hexane

Sources & evidence

ORD record
ord-2579188a129a464ab81ca5a0cf5d57e5
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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