((2S,3R)-3-Undecyloxiran-2-yl)methanol → (R)-1,3-dihydroxytetradecane

HRID 233468ノート

反応式

HRID 233468 の反応式
[O:1]1[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:2]1[CH2:3][OH:4].COCCO[AlH2-]OCCOC.[Na+]>O1CCCC1>[OH:1][C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:2][CH2:3][OH:4]

参加物

4

反応物 2

HCID 9877949((2S,3R)-3-Undecyloxiran-2-yl)methanolHCID 16684438Red-Al

生成物 1

HCID 11791041(R)-1,3-dihydroxytetradecane収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of epoxide 8 (9.00 g, 40 mmol) in tetrahydrofuran (80 mL) at -20° C. was added a solution of Red-Al (40 mL, 3M) and the reaction temperature was slowly raised to 0° C. and subsequently to room temperature and stirred for 12 h. After completion of the reaction (TLC), the excess of Red-Al was quenched with methanol (10 mL) and poured in to a conical flask containing ethyl acetate (400 mL) and rochelle salt solution (100 mL) and stirred for 2 h until clear separation of two layers occurred. The organic layer was separated, dried and concentrated to give the diol 9 as a colorless solid (8.1 g, 89%). m.p. 59°-60° C.

後処理

  1. customAfter completion of the reaction (TLC)
  2. customthe excess of Red-Al was quenched with methanol (10 mL)
  3. additionpoured in to a conical flask
  4. additioncontaining ethyl acetate (400 mL) and rochelle salt solution (100 mL)
  5. stirringstirred for 2 h until clear separation of two layers
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-9bd9a246afc1474c8cbb4f19b3d10e65
出典データセット
uspto-grants-1997_01
特許番号
US05593969

反応ノート

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