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

HRID 710359ノート

反応式

HRID 710359 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 152893643-(1-Adamantyl)-4-methoxyphenylacetylene収率 44.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-583b2cbe0e25486ab26c343936270957
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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