Cyclopentanol → (4-Cyclopentyloxy-3-methoxy-phenyl)-acetic acid methyl ester

HRID 1063816ノート

反応式

HRID 1063816 の反応式
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:26][O:27][C:28](=[O:39])[CH2:29][C:30]1[CH:35]=[CH:34][C:33](O)=[C:32]([O:37][CH3:38])[CH:31]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:26][O:27][C:28](=[O:39])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:32]([O:37][CH3:38])[CH:31]=1

参加物

6

反応物 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 85214Methyl 4-hydroxy-3-methoxyphenylacetateHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 23402498(4-Cyclopentyloxy-3-methoxy-phenyl)-acetic acid methyl ester収率 66.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Cyclopentanol (7.7 ml, 85 mmol) and triphenylphosphine (28 g, 107 mmol) were added to a solution of (4-hydroxy-3-methyoxy-phenyl)-acetic acid methyl ester (14 g, 71 mmol) in tetrahydrofuran (280 ml) under nitrogen at 0° C. Diethylazodicarboxylate (15.7 ml, 100 mmol) was then added dropwise and the reaction was allowed to warm to room temperature and stirred for 44 hours. The solvent was removed under reduced pressure, pentane (200 ml) was added and the suspension was filtered. The filtrate was concentrated under reduced pressure and purified by flash column chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (90:10 changing to 85:15, by volume) to give (4-cyclopentyloxy-3-methoxy-phenyl)-acetic acid methyl ester (12.4 g) as a colourless oil. 1H NMR (400 MHz, CD3OD): δ=6.79-6.85 (2H, m), 6.73-6.79 (1H, d), 4.73-4.79 (1H, brs), 3.79 (3H, s), 3.64 (3H, s), 3.53 (2H, s), 1.74-1.89 (6H, m), 1.56-1.67 (2H, m) ppm. LRMS (electrospray): m/z [M+Na]+ 287. Anal. Found C, 68.01; H, 7.74. C15H20O4 requires C, 68.16; H, 7.63%.

後処理

  1. customThe solvent was removed under reduced pressure, pentane (200 ml)
  2. additionwas added
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by flash column chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (90:10 changing to 85:15, by volume)

出典と根拠

ORDレコード
ord-163dcd96946e4e8a99647e5b9adeb967
出典データセット
uspto-grants-2005_11
特許番号
US06967204B2

反応ノート

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