Hydrochloric Acid → HCID 54313026、化合物

HRID 1296858ノート

反応式

HRID 1296858 の反応式
C([O:4][CH2:5][CH:6]=[C:7]([CH3:16])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:15])[C:12]([OH:14])=[O:13])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.Cl>CO.O>[OH:4][CH2:5][CH:6]=[C:7]([CH3:16])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:15])[C:12]([OH:14])=[O:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 76842371HCID 76842371、化合物

生成物 1

HCID 54313026HCID 54313026、化合物収率 59.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a solution of acid 232a (20.0 g, 88.4 mmol) in 400 mL of methanol was added a solution of potassium carbonate (24.4 g, 177 mmol) in 100 mL of water. The resulting mixture was vigorously stirred overnight at room temperature. The reaction was cooled to 0° C., methylene chloride (200 mL) was added, and the aqueous layer was acidified to pH 3 with 1 M HCl. The organic layer was separated, and the aqueous layer was extracted with methylene chloride (2×200 mL). The combined organic extracts were washed with brine, dried over MgSO4, and reduced to dryness in vacuo. The crude product (9.65 g, 52.4 mmol, 59% yield) was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ: 6.86 (t of q, J=7.25 Hz, J=1.50 Hz, 1H, ═CH), 5.43 (t of q, J=7.00 Hz, J=1.50 Hz, 1H, ═CH), 4.16 (d, J=7.00 Hz, 2H, —CH2O—), 2.33 (q, J=7.50 Hz, 2H, —CH2—), 2.16 (t, J=7.50 Hz, 2H, —CH2—), 1.83 (s, 3H, —CH3), 1.68 (s, 3H, —CH3). LC/MS (ESI): m/z 207 [M+Na]+.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (2×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4

出典と根拠

ORDレコード
ord-a82847623c424475904fd37c0a922e59
出典データセット
uspto-grants-2007_07
特許番号
US07247752B2

反応ノート

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