Acetylene → HCID 15405342, compound

HRID 1952705Notes

Reaction equation

HRID 1952705 reaction equation
C#C.[C:3](O[K])(C)(C)[CH3:4].[CH2:9]1[C:13]2([CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]2)[CH2:12][CH2:11][CH2:10]1.[NH4+].[Cl-]>C1COCC1>[C:3]([C:15]1([OH:19])[CH2:16][CH2:17][CH2:18][C:13]2([CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:14]1)#[CH:4]

Participants

6

Reactant 4

HCID 6326AcetyleneHCID 25517Ammonium ChlorideHCID 10888101spiro[4.5]decan-7-oneHCID 178418922HCID 178418922, compound

Product 1

HCID 15405342HCID 15405342, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Acetylen was bubbled for 30 mn through a mixture of tBuOK (14.11 g, 125.8 mmol, 1.1 equiv) in THF (100 ml) cooled to 0° C. The resulting white suspension was diluted with more THF (50 ml) and treated with spiro[4.5]decan-7-one (1) (17.20 g, 113.2 mmol) added dropwise for 20 mn. The reaction mixture was stirred at room temperature for 3 h, treated with saturated NH4Cl (500 ml) and extracted with MTBE (4×150 ml). The combined organic phases were washed with H2O (6×70 ml) until neutral pH and dried over MgSO4. 16.90 g (84%) of crude product (2) was isolated as an orange oil that was used without further purification in the following step.

Workup

  1. additionadded dropwise for 20 mn
  2. extractionextracted with MTBE (4×150 ml)
  3. washThe combined organic phases were washed with H2O (6×70 ml) until neutral pH
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-bc7fc9aed00346939d6e6d0299a45d6d
Source dataset
uspto-grants-2000_09
Patent number
US06114300

Reaction notes

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