Benzyl Bromide → 6-Fluoro-7-benzyloxychroman-4-one

HRID 1384321ノート

反応式

HRID 1384321 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][C:5]2=[O:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:13]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 211866006-fluoro-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

生成物 1

HCID 211865906-Fluoro-7-benzyloxychroman-4-one収率 73%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 6-fluoro-7-hydroxychroman-4-one (the compound of Preparation 29, 0.93 g, 5.11 mmol), benzyl bromide (0.61 mL, 5.13 mmol), potassium carbonate (1.41 g, 10.2 mmol) in acetone (100 mL) was stirred at ambient temperature overnight. The mixture was cooled, filtered, and concentrated to a yellow solid. This residue was recrystallized from ethyl acetate/ether to give 1.02 g (73%) of 6-fluoro-7-benzyloxychroman-4-one in two crops as cream white crystals which had: mp 155-156° C.; NMR δ7.58 (d, J=11 Hz, 1 H), 7.46-7.33 (m, 5 H), 6.54 (d, J=6.7 Hz, 1 H), 5.16 (d, 2 H), 4.50 (t, J=6.4 Hz, 2 H), 2.75 (t, J=6.4 Hz, 2 H). Analysis calculated for C16H13FO2: C, 70.58; H, 4.81. Found: C, 70.45; H, 4.80.

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to a yellow solid
  4. customThis residue was recrystallized from ethyl acetate/ether

出典と根拠

ORDレコード
ord-6835b40a682e40d0a3c9b9a1b3ad3184
出典データセット
uspto-grants-2001_07
特許番号
US06258827B1

反応ノート

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