2-Butyne-1,4-diol → HCID 178501074, compound

HRID 1893358Notes

Reaction equation

HRID 1893358 reaction equation
Cl[C:2](=[N:13][OH:14])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.[CH2:15]([OH:20])[C:16]#[C:17][CH2:18][OH:19].C(N(CC)CC)C>ClCCCl.C[C]1[C](C)[C](C)[C](C)[C]1C.C1CC=CCCC=C1.Cl[Ru]>[CH3:12][O:11][C:9]([C@H:6]1[CH2:7][CH2:8][C@H:3]([C:2]2[C:17]([CH2:18][OH:19])=[C:16]([CH2:15][OH:20])[O:14][N:13]=2)[CH2:4][CH2:5]1)=[O:10]

Participants

6

Reactant 3

HCID 80662-Butyne-1,4-diolHCID 8471TriethylamineHCID 178501086HCID 178501086, compound

Product 1

HCID 178501074HCID 178501074, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178420236HCID 178420236, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of trans-methyl 4-(chloro(hydroxyimino)methyl)cyclohexanecarboxylate (0.900 g, 4.10 mmol) and but-2-yne-1,4-diol (0.370 g, 4.30 mmol) in 1,2-dichloroethane (41.0 ml) was added chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium(II) (0.0778 g, 205 μmol) and triethylamine (0.713 ml, 5.12 mmol) at room temperature. The reaction mixture was stirred for 20 h. The solvent was evaporated. The residue was triturated in ethyl acetate (50 ml). The solids were removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. Flash chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.758 g, 69%) as light brown oil.

Workup

  1. customThe solvent was evaporated
  2. customThe residue was triturated in ethyl acetate (50 ml)
  3. customThe solids were removed by filtration
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8806997d46b8432b848ed0e81dda8efa
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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