Triphenylphosphine → [4-(Tetrahydro-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester

HRID 23533

反応式

HRID 23533 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37](=[O:50])[NH:38][C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([OH:49])=[CH:41][CH:40]=1)([CH3:35])([CH3:34])[CH3:33].[O:51]1[CH2:56][CH2:55][CH:54](O)[CH2:53][CH2:52]1>C1COCC1>[C:32]([O:36][C:37](=[O:50])[NH:38][C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([O:49][CH:54]2[CH2:55][CH2:56][O:51][CH2:52][CH2:53]2)=[CH:41][CH:40]=1)([CH3:35])([CH3:33])[CH3:34]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 5462977Diethyl azodicarboxylateHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

生成物 1

HCID 20756580[4-(Tetrahydro-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Triphenylphosphine (2.8 g, 10.8 mmol) was dissolved in THF (5 mL) and cooled to 0° C. To this colorless solution diethylazodicarboxylate (1.9 grams, 10.8 mmol) was added dropwise to afford an orange solution. After 15 min at 0° C., a copious precipitate had formed. 4-Hydroxy-naphthalen-1-yl-carbamic acid tert-butyl ester (934 mg, 3.6 mmol) and tetrahydro-4H-pyran-4-ol (552 mg, 5.4 mmol) were then added in one portion as a solution in 2 mL of THF. The purple suspension was stirred at 0° C. for one h then at room temperature for 48 h. The solvent was then evaporated and chromatographed on silica gel (40% EtOAc-hexanes) to provide 680 mg (55%) of [4-(tetrahydro-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester as a purple solid.

後処理

  1. customto afford an orange solution
  2. customa copious precipitate had formed
  3. waitat room temperature for 48 h
  4. customThe solvent was then evaporated
  5. customchromatographed on silica gel (40% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-3ce72494a05e4cd89083727714415d7a
出典データセット
uspto-grants-2005_02
特許番号
US06852717B2

関連ノート

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