Ethylparaben → HCID 65018987、化合物

HRID 2261221ノート

反応式

HRID 2261221 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.O[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:17]1[CH2:18][CH2:19][CH:14]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:15][CH2:16]1

参加物

6

反応物 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylate

生成物 1

HCID 65018987HCID 65018987、化合物収率 61.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

An ice-cold solution of ethyl 4-hydroxybenzoate (0.82 g), 4-hydroxy-tetrahydro-2H-pyran (0.5 g) and triphenylphosphine in THF (50 ml) was treated dropwise with diisopropyl azodicarboxylate (1.69 ml). After 15 min the cooling bath was removed and the reaction stood overnight at rt. The mixture was evaporated, redissolved in toluene and successively washed with 2N sodium hydroxide (2×20 ml), water (2×20 ml) and brine (20 ml). After drying (magnesium sulfate) the solution was loaded directly on to a silica flash column (step gradient 10-30% EtOAc in light petroleum 40-60) to give the title compound (D5) (0.75 g). 1H NMR δ (CDCl3): 7.98 (2H, d, J=8.5Hz), 6.91 (2H, d, J=8.5 Hz), 4.60 (1H, m), 4.35 (2H, q, J=9.8 Hz), 3.98 (2H, m), 3.57 (2H, m), 2.05 (2H, m), 1.80 (2H, m), 1.38 (3H, t, J=9.8 Hz).

後処理

  1. customAfter 15 min the cooling bath was removed
  2. customThe mixture was evaporated
  3. dissolutionredissolved in toluene
  4. washsuccessively washed with 2N sodium hydroxide (2×20 ml), water (2×20 ml) and brine (20 ml)
  5. dry with materialAfter drying (magnesium sulfate) the solution

出典と根拠

ORDレコード
ord-d8a1df2603954e71945435b58964bb22
出典データセット
uspto-grants-2010_12
特許番号
US07846922B2

反応ノート

読み込み中…