Allyl bromide → (+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol

HRID 2116060ノート

反応式

HRID 2116060 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([OH:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C.[CH2:26]([O:29]CC=C)[CH:27]=[CH2:28].C(C1C=CC=C(C2C=CC(Cl)=CC=2C)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O>C1(C)C=C(C)C=C(C)C=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[O:14][CH:27]([CH2:26][OH:29])[CH2:28][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:15])[CH:3]=1

参加物

8

反応物 6

HCID 7841Allyl bromideHCID 11194Diallyl etherHCID 11430Potassium Carbonate2 回HCID 70297m-Chloroperbenzoic acidHCID 532185934'-Chloro-2'-methyl[1,1'-biphenyl]-2-olHCID 689641103-Allyl-4'-chloro-2'-methyl-1,1'-biphenyl-2-ol2 回

生成物 1

HCID 68964315(+/-)-[7-(4-Chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol収率 61%

試薬・触媒・溶媒 1

HCID 7947Mesitylene溶媒

実験手順

Treatment of 4′-chloro-2′-methyl-1,1′-biphenyl-2-ol (4.54 g, 20.78 mmol) with potassium carbonate (11.47 g, 83.04 mmol) and allyl bromide (3.01 g, 24.91 mol), followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 provided 3-allyl-4′-chloro-2′-methyl-1,1′-biphenyl-2-ol. Treatment of 3-allyl-4′-chloro-2′-methyl-1,1′-biphenyl-2-ol (4.5 g, 17.39 mmol) with 3-chloroperoxybenzoic acid (12.0 g, 69.57 mmol, 77%) followed by potassium carbonate (6.0 g, 43.48 mmol) generally according to the procedure described for Intermediate 9 afforded 2.9 g (61%) of (±)-[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol as a colorless oil. Anal. calcd. for C16H15ClO2: C, 69.95; H, 5.5. Found: C, 69.23; H, 5.42.

出典と根拠

ORDレコード
ord-e3c1b597983440ce9d4f0b921961b64f
出典データセット
uspto-grants-2008_10
特許番号
US07435837B2

反応ノート

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