Triethylamine → Naphthalene-2-yl-propynoic acid ethyl ester

HRID 24018

反応式

HRID 24018 の反応式
S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:36]([O:38][C:39](=[O:53])[CH2:40][C:41]([C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)=O)[CH3:37].C(N(CC)CC)C>ClCCCl>[CH2:36]([O:38][C:39](=[O:53])[C:40]#[C:41][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)[CH3:37]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 27601583-Naphthalen-2-yl-3-oxopropionic acid ethyl ester

生成物 1

HCID 66819016Naphthalene-2-yl-propynoic acid ethyl ester収率 42.7%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

Triflic anhydride (2.9 mL, 17 mmol) was added dropwise to a solution of triphenylphosphine oxide (4.8 g, 17 mmol) in 1,2-dichloroethane (40 mL) at 0° C. The resulting suspension was stirred for 15 minutes, followed by the dropwise addition of a solution of 3-naphthalen-2-yl-3-oxo-propionic acid ethyl ester (3.2 g, 12 mmol) in 1,2-dichloroethane (40 mL). After the addition was complete, triethylamine (4.0 mL, 29 mmol) was added and the reaction mixture was heated at reflux for 1 hr. The solution was cooled to room temperature, washed with water, and dried (MgSO4). The solvent was removed under reduced pressure, and the product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1) to yield naphthalene-2-yl-propynoic acid ethyl ester (1.15 g, 37% yield) as a yellow oil. 1H NMR (CDCl3) δ 8.25 (s, 1H), 7.95 (m, 3H), 7.66 (m, 3H), 4.46 (m, 2H), 1.51 (t, 3H, J=8.0 Hz).

後処理

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 1 hr
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1)

出典と根拠

ORDレコード
ord-31126ea1635145a9b5623050008ac4fc
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

関連ノート

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