Proton sponge → 1-(Isocyanatomethyl)-4-(propan-2-yloxy)benzene

HRID 852287

反応式

HRID 852287 の反応式
CN(C)[C:3]1[C:12]2[C:7](=CC=C[C:11]=2[N:13]([CH3:15])C)[CH:6]=[CH:5][CH:4]=1.[CH:17]([O:20]C1C=CC(CC(O)=O)=CC=1)([CH3:19])[CH3:18].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>O1CCCC1>[N:13]([CH2:11][C:12]1[CH:3]=[CH:4][C:5]([O:20][CH:17]([CH3:19])[CH3:18])=[CH:6][CH:7]=1)=[C:15]=[O:38]

参加物

5

反応物 3

HCID 88675Proton spongeHCID 199401P,P-Diphenylphosphinic azideHCID 799528Benzeneacetic acid, 4-(1-methylethoxy)-

生成物 1

HCID 574300951-(Isocyanatomethyl)-4-(propan-2-yloxy)benzene収率 112.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1,8-Bis(dimethylamino)-naphtalene (3.19 g, 14.9 mmol) was added to a solution of 4-(isopropoxy)phenyl acetic acid (2.89 g, 14.9 mmol) in dry tetrahydrofuran (18 mL) at rt under argon atmosphere. After 25 minutes stirring at rt diphenylphosphoryl azide (4.10 g, 14.9 mmol) was added dropwise and the mixture refluxed for 6 hours. It was allowed to cool to rt and then stored at −20° C. overnight to precipitate out the ammonium phosphate salt. A mixture of diethyl ether and ethyl acetate (1:1 v/v, 25 mL) was added to the cold reaction mixture. The precipitate was filtered from the reaction mixture and washed with diethyl ether:ethyl acetate (1:1 v/v, 20 mL). The filtrate was evaporated to dryness giving 1-isocyanatomethyl-4-isopropoxybenzene as an oil (3.2 g), which was used in the next step without further purification.

後処理

  1. additionwas added dropwise
  2. temperaturethe mixture refluxed for 6 hours
  3. customto precipitate out the ammonium phosphate salt
  4. additionA mixture of diethyl ether and ethyl acetate (1:1 v/v, 25 mL)
  5. additionwas added to the cold reaction mixture
  6. filtrationThe precipitate was filtered from the reaction mixture
  7. washwashed with diethyl ether:ethyl acetate (1:1 v/v, 20 mL)
  8. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-64e9399581e34879b902cfad5fac08f1
出典データセット
uspto-grants-2007_08
特許番号
US07253186B2

関連ノート

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