Hydrochloric Acid → trans-4-(1-Pentenylcyclohexyl)-3-fluorophenylboronic acid

HRID 1929261ノート

反応式

HRID 1929261 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H]2CC[C@H](C=CCCC)CC2)[CH:5]=[CH:6][CH:7]=1.[CH:19]([Li])([CH2:21][CH3:22])[CH3:20].C[O:25][B:26]([O:29]C)OC.Cl.[C:32]1([CH3:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C1CCCCC1.CCCCCC>[CH:38](/[C:32]1([C:3]2[CH:4]=[CH:5][C:6]([B:26]([OH:29])[OH:25])=[CH:7][C:2]=2[F:1])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[CH:20]\[CH2:19][CH2:21][CH3:22]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8470Trimethyl borateHCID 178418400CID 53628100HCID 178444322HCID 178444322、化合物

生成物 1

HCID 68419934trans-4-(1-Pentenylcyclohexyl)-3-fluorophenylboronic acid

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8078Cyclohexane溶媒

実験手順

The compound (40) (15.8 g) and THF (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to −74° C. sec-Butyllithium (1.00 M, in a n-hexane and cyclohexane solution; 20.0 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the mixture was stirred for another 2 hours. Subsequently, trimethoxyborane (7.3 g) in a THF solution (40 ml) was added dropwise thereto in the temperature range of −75° C. to −70° C., and the mixture was stirred for 8 hours while allowing the temperature to come to 25° C. The reaction mixture obtained was poured into an aqueous 1N—HCl solution (200 ml), and mixed. Then, toluene (200 ml) was added thereto and the mixture was allowed to be separated into organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with brine, and then dried over anhydrous magnesium sulfate. The solution obtained was washed with heptane and dried, giving 5.5 g of trans-4-(1-pentenylcyclohexyl)-3-fluorophenylboronic acid (41). The yield based on the compound (40) was 29.6%.

後処理

  1. addition20.0 ml) was added dropwise
  2. stirringin the temperature range of −75° C. to −70° C., and the mixture was stirred for 8 hours
  3. customto come to 25° C
  4. customThe reaction mixture obtained
  5. additionmixed
  6. customto be separated into organic and aqueous phases
  7. customThe organic phase obtained
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solution obtained
  11. washwas washed with heptane
  12. customdried

出典と根拠

ORDレコード
ord-88d30d4d40764b8388c9251b7139a1ae
出典データセット
uspto-grants-2012_05
特許番号
US08187494B2

反応ノート

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