Water → HCID 13746901, compound

HRID 1732025

Reaction equation

HRID 1732025 reaction equation
CO[C:3]([O:11]C)([O:9][CH3:10])[CH2:4][CH2:5][CH2:6][C:7]#[CH:8].C([Li])CCC.[CH2:18]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1.CCCCCC>[OH:28][CH:27]([C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]#[C:7][CH2:6][CH2:5][CH2:4][C:3]([O:9][CH3:10])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 100129102-BenzylbenzaldehydeHCID 130965676,6,6-Trimethoxyhex-1-yneHCID 178418339Butyllithium

Product 1

HCID 13746901HCID 13746901, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred mixture of 2.19 g (12.73 mmol) 1,1,1-trimethoxy-5-hexyne in 15 ml dry tetrahydrofuran (THF) at -78° under nitrogen was added 8.37 ml of 1.52M n-butyllithium (12.73 mmol) in hexane dropwise. The mixture was stirred at -78° for 1 hour and 2.0 g of 2-benzylbenzaldehyde (10.20 mmol) in 10 ml dry THF was added dropwise at -78°. The mixture was stirred at room temperature for 12 hours and poured into water. The reaction mixture was extracted with ether (2×75 ml) and the combined organic layers were washed with water (50 ml), saturated sodium chloride (50 ml), and dried (MgSO4). Filtration and evaporation left an oil that was purified by flash chromatography to give the title compound in 56% yield (2.02 g). NMR (CDCl3, 200 MHz) δ: 1.80 (m, 2H), 2.25-2.50 (m, 5H), 3.67 (s, 3H), 4.18 (br s, 2H), 5.60 (s, 1H), 7.12-7.75 (m, 9H). Mass spectrum: m/z=322 (M+).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionThe reaction mixture was extracted with ether (2×75 ml)
  3. washthe combined organic layers were washed with water (50 ml), saturated sodium chloride (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation
  6. waitleft an oil that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-13e82e3a0ed34d6a81e2bcd79eb8fcbe
Source dataset
uspto-grants-1986_11
Patent number
US04624964

Linked notes

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