Triethylamine → HCID 22452629、化合物

HRID 2185881ノート

反応式

HRID 2185881 の反応式
[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([NH2:14])=O)[C:3]=1[O:15][CH3:16].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:12]([C:4]1[C:3]([O:15][CH3:16])=[C:2]([I:1])[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)#[N:14]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 22452681HCID 22452681、化合物

生成物 1

HCID 22452629HCID 22452629、化合物収率 100.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred, cooled (0° C.) suspension of 4-iodo-3-methoxy-5,6,7,8-tetrahydro-2-naphthalenecarboxamide (2.06 g, 6.22 mmol), triethylamine (2.77 mL, 19.91 mmol), and THF (40 mL) was added trifluoroacetic anhydride (1.23 mL, 8.71 mmol) dropwise via syringe. After addition, the ice bath was removed and the reaction stirred overnight at ambient temperature. The mixture was cooled to 0° C. and excess trifluoroacetic anhydride destroyed with H2O (2 mL). Ethyl acetate (50 mL) was added and the organic layer was washed with H2O (3×25 mL) and brine (25 mL), dried (NaSO4), filtered, concentrated in vacuo and purified by chromatography (100% DCM) to afford a light brown solid (1.96 g, 100%). 1H NMR (CDCl3) δ 7.29 (s, 1H), 4.0 (s, 3H), 2.74 (m, 4H), 1.76 (m, 4H), MS m/z 314 (M+H).

後処理

  1. temperatureTo a stirred, cooled
  2. additionAfter addition
  3. customthe ice bath was removed
  4. temperatureThe mixture was cooled to 0° C.
  5. customexcess trifluoroacetic anhydride destroyed with H2O (2 mL)
  6. additionEthyl acetate (50 mL) was added
  7. washthe organic layer was washed with H2O (3×25 mL) and brine (25 mL)
  8. dry with materialdried (NaSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified by chromatography (100% DCM)

出典と根拠

ORDレコード
ord-2f04be89c25841d884870ddf74d9735d
出典データセット
uspto-grants-2002_06
特許番号
US06403601B1

反応ノート

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