Water → HCID 5252223, compound

HRID 1176176Notes

Reaction equation

HRID 1176176 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:10]([C:22]#[C:23][Si](C)(C)C)=[CH:9][C:8]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])(C)C.[OH-].[Na+].O>C1COCC1.CO>[C:6]([C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:10]([C:22]#[CH:23])=[CH:9][C:8]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])#[CH:5]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68408471HCID 68408471, compound

Product 1

HCID 5252223HCID 5252223, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,4-Bis(trimethylsilylethynyl)-2,5-di-n-octyloxybenzene (2.331 g, 4.42×10−3 mol) was dissolved in a mixture of THF (25 ml) and MeOH (25 ml). 5N NaOH (2.0 ml, 1.0×10−2 mol) was added and the solution was stirred for 3 h under Ar. Water was added to the reaction mixture. The organic layer was extracted three times with CHCl3. The combined organic layers were dried over Na2SO4. The residue was chromatographed on silica gel with 1:1 hexane:CHCl3 as the eluent. Yield=1.419 g (84% based on 2.331 g of 1,4-bis(trimethylsilylethynyi)-2,5-di-n-octyloxybenzene). 1H NMR (300 MHz, CDCl3): δ 6.95 (s, 2H, Ph-H), 3.97 (t, 8H, J=6.6 Hz, —OCH2—), 3.33 (s, 2H, —CC—H), 1.80 (quint, 4H, J=7.0 Hz, —OCH2CH2—), 1.39-1.52 (m, 4H, —OCH2CH2CH2—), 1.15-1.39 (m, 16H, —CH2—), 0.88 (t, 6H, J=6.7 Hz, —CH3). CI MS m/z: 382.285 (M+) (calcd 382.287).

Workup

  1. extractionThe organic layer was extracted three times with CHCl3
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customThe residue was chromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-22fbe66d9ced4a2b8dcc88c775e93bf3
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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