Sodium borohydride → HCID 10902156、化合物

HRID 582902ノート

反応式

HRID 582902 の反応式
[O:1]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[C:3](OC)=[O:4].[BH4-].[Na+]>O1CCCC1>[O:1]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[CH2:3][OH:4]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 56999066HCID 56999066、化合物

生成物 1

HCID 10902156HCID 10902156、化合物収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In 500 ml of tetrahydrofuran were suspended 62.4 g (0.2 mol) of the methyl (2S,3R)-2,3-epoxyoctadecanoate (V-1) prepared in Example 3-(3) and 7.4 g (0.2 mol) of NaBH4, followed by heat refluxing for 3 hours. After confirming disappearance of the compound (V-1) by TLC, tetrahydrofuran was evaporated. To the residue were added 20 ml of water and then 500 ml of a saturated ammonium chloride aqueous solution to adjust to pH 5 to 6, and the mixture was extracted with 500 ml of ethyl acetate. After drying, ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from heptane to obtain 42.6 g (0.15 mol; yield: 75%) of (2R,3R)-2,3-epoxyoctadecanol (melting point: 77 to 78° C.). Optical rotation [α]D25 =+24.5° (c=0.285, CHCl3)

後処理

  1. temperatureby heat
  2. temperaturerefluxing for 3 hours
  3. customwas evaporated
  4. additionTo the residue were added 20 ml of water
  5. extractionthe mixture was extracted with 500 ml of ethyl acetate
  6. customAfter drying
  7. customethyl acetate was removed by evaporation
  8. customthe resulting crude crystals were recrystallized from heptane

出典と根拠

ORDレコード
ord-0b1b40ca4bb641a3a0d2421a717da038
出典データセット
uspto-grants-1999_07
特許番号
US05925792

反応ノート

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