Acetylene → 2-Ethynyldecahydronaphthalen-2-ol

HRID 634980Notes

Reaction equation

HRID 634980 reaction equation
C#C.[C:3](O[K])(C)(C)[CH3:4].[CH2:9]1[CH2:19][CH:18]2[CH:12]([CH2:13][C:14]([CH2:16][CH2:17]2)=[O:15])[CH2:11][CH2:10]1>C1COCC1>[C:3]([C:14]1([OH:15])[CH2:16][CH2:17][CH:18]2[CH:12]([CH2:11][CH2:10][CH2:9][CH2:19]2)[CH2:13]1)#[CH:4]

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 1003282-DecaloneHCID 178418922HCID 178418922, compound

Product 1

HCID 212616182-Ethynyldecahydronaphthalen-2-olYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetylene was bubbled for 4 hours through a mixture of tBuOK (95.8 g, 0.85 mol) in THF (11) at 0° C. 2-Decalone (100 g, 0,66 mol) was added slowly at RT to the slightly yellow suspension and the resulting mixture was stirred for additional 3.5 hours, quenched with saturated NH4Cl (500 ml) solution, and extracted with MTBE (2×700 ml). The combined organic phases were washed with NH4Cl (500 ml), H2O (2×500 ml), saturated NaCl (500 ml) solution until neutral pH was achieved, dried (MgSO4), and concentrated in vacuo. The crude orange oil was flash distilled (0.01 Torr, 88-90° C.) yielding 100.6 g (86%) of 2-ethynyldecahydro-naphthalen-2-ol.

Workup

  1. customquenched with saturated NH4Cl (500 ml) solution
  2. extractionextracted with MTBE (2×700 ml)
  3. washThe combined organic phases were washed with NH4Cl (500 ml), H2O (2×500 ml), saturated NaCl (500 ml) solution until neutral pH
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. distillationdistilled (0.01 Torr, 88-90° C.)

Sources & evidence

ORD record
ord-a157331c8c8b47179dfdbd0bcf7692ea
Source dataset
uspto-grants-2001_02
Patent number
US06184419B2

Reaction notes

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