Triphenylphosphine → 6-(2-Cyclopropylethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63089

反応式

HRID 63089 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[CH:13]1([CH2:16][CH2:17]O)[CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:13]1([CH2:16][CH2:17][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH2:15][CH2:14]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 1376422-Cyclopropylethan-1-olHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 655990986-(2-Cyclopropylethoxy)-1,2,3,4-tetrahydronaphthalen-1-one収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (1.0 g, 6.0 mmol), 2-cyclopropylethanol (640 mg, 7.0 mmol) and triphenylphosphine (3.25 g, 12 mmol) in THF (100 mL) was added DEAD (2.13 g, 12 mmol) at 0° C. The reaction was stirred at rt overnight. The solution was concentrated and purified by silica gel chromatography (PE:EtOAc=12:1) to give 470 mg (33%) of the title compound as a red oil. 1H NMR (300 MHz, CDCl3): δ 0.13-0.15 (2H, m), 0.50-0.52 (2H, m), 0.86-0.93 (1H, m), 1.68-1.74 (2H, m), 2.11-2.15 (2H, m), 2.64 (2H, t, J=6.3 Hz), 2.93 (2H, t, J=6.0 Hz), 4.10 (2H, t, J=6.6 Hz), 6.73 (1H, s), 6.83 (1H, dd, J=2.4, 8.7 Hz), 8.02 (1H, d, J=8.7 Hz).

後処理

  1. concentrationThe solution was concentrated
  2. custompurified by silica gel chromatography (PE:EtOAc=12:1)

出典と根拠

ORDレコード
ord-e0b78794a7114837b8a773ee7e78cf55
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

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