Potassium Carbonate → 3-(1-Adamantyl)-4-methoxyphenylacetylene

HRID 710359Notes

Reaction equation

HRID 710359 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH:14]=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:21]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]12([C:11]3[CH:12]=[C:13]([C:14]#[CH:21])[CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 540295304-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 152893643-(1-Adamantyl)-4-methoxyphenylacetyleneYield 44.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(1-admantanyl)-4-methoxybenzaldehyde (0.12 g, 0.42 mmol), dimethyl(1-diazo-2-oxopropyl)phosphonate (0.097 g, 0.51 mmol) and K2CO3 (0.069 g, 0.5 mmol) in anhydrous MeOH (5 ml) was stirred overnight at 80° C. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc, washed with H2O, dried over MgSO4 and filtered. The filtrate was passed through SiO2 bead and the filtrate was evaporated to dryness to give the title product (0.05 g; 42%), which was used for the next step without purification. 1H-NMR (CDCl3) 1.75 (s, 3H); 2.05 (broad s, 9H); 2.96 (s, 1H); 3.82 (s, 3H); 6.77 (d, 1H, J=8.31 Hz); 7.29-7.34 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-583b2cbe0e25486ab26c343936270957
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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