Water → (6-Methyl-[1,1'-biphenyl]-3-yl)methanol

HRID 270005

反応式

HRID 270005 の反応式
I[C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:7]1[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][C:4]([CH2:9][OH:10])=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 51667983-Iodo-4-methylbenzyl alcohol

生成物 1

HCID 23089113(6-Methyl-[1,1'-biphenyl]-3-yl)methanol収率 88.2%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 10311-Propanol溶媒

反応条件

温度
100 °C

実験手順

To a mixture of compound PPP, (3-iodo-4-methyl-phenyl)-methanol, (4 g, 16.12 mmol) and phenylboronic acid (2.06 g, 16.89 mmol) in 1-propanol (30 mL) was successively added palladium(II) acetate (0.01276 g, 0.05 mmol), triphenyl phosphine (0.042 g, 0.161 mmol), aq. sodium carbonate solution (2 M, 11.44 mL, 22.88 mmol), and water (6 mL). The mixture was heated to 100° C. until reaction is complete (tlc), cooled, quenched with water (20 mL) and extracted into ethyl acetate (3×50 mL). Combined organic layer was washed with 2% aq. sodium bicarbonate (2×25 mL), brine (1×50 mL), dried (MgSO4) and concentrated to yield 2.82 g of (6-methyl-biphenyl-3-yl)-methanol, compound QQQ, that was directly taken into next step without any further purification; Rt: 10.95 min.

後処理

  1. temperaturecooled
  2. customquenched with water (20 mL)
  3. extractionextracted into ethyl acetate (3×50 mL)
  4. washCombined organic layer was washed with 2% aq. sodium bicarbonate (2×25 mL), brine (1×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-317df5cd4eb34632a371a9c245d9c4e2
出典データセット
uspto-grants-2008_11
特許番号
US07449481B2

関連ノート

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