Hydrochloric Acid → (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal

HRID 703681ノート

反応式

HRID 703681 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:9][C:10](OC(C)(C)C)=[O:11].CC(C[AlH]CC(C)C)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:9][CH:10]=[O:11]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 86743988t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate

生成物 1

HCID 14852578(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-75 °C

実験手順

(1J.a) 9.2 g of t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate are dissolved in 115 ml of toluene while gassing with argon and with the exclusion of moisture and cooled to -75° C. 26.5 ml of a 1.2M DIBAH solution in toluene are then added dropwise within 1/2 hour in such as manner that the temperature does not exceed -70° C. The mixture is stirred at -75° C. for a further one hour. There are then added dropwise 7.4 ml of saturated ammonium chloride solution and subsequently 15.5 ml of 1N hydrochloric acid at -70° C. The cooling bath is removed and the mixture is left to warm to room temperature. After stirring at room temperature for one hour the organic phase is separated and washed with water. The organic phase is dried, filtered and evaporated. The material obtained is chromatographed on silica gel. There is obtained [(R)-3-[(tetrahydro-2H-pyran-2-yl)oxyl]tetradecanal as a colourless oil.

後処理

  1. customdoes not exceed -70° C
  2. customThe cooling bath is removed
  3. waitthe mixture is left
  4. temperatureto warm to room temperature
  5. stirringAfter stirring at room temperature for one hour the organic phase
  6. customis separated
  7. washwashed with water
  8. customThe organic phase is dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe material obtained
  12. customis chromatographed on silica gel

出典と根拠

ORDレコード
ord-7d1c028bb53e4cbca227ca28d9a605b3
出典データセット
uspto-grants-1991_01
特許番号
US04983746

反応ノート

読み込み中…