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Acetic Acid → Tert-butyl 6-triphenylmethyloxy-3,5-dihydroxyhexanoate

HRID 1594450
ノート
印刷プレビュー

反応式

HRID 1594450 の反応式
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:8][CH2:9][CH:10]([OH:22])[CH2:11][C:12](=[O:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[BH4-].[Na+].C(O)(=O)C>C1COCC1.O>[C:29]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:8][CH2:9][CH:10]([OH:22])[CH2:11][CH:12]([OH:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 19778647Tert-butyl 6-triphenylmethyloxy-5-hydroxy-3-oxohexanoate

生成物 1

HCID 11374654Tert-butyl 6-triphenylmethyloxy-3,5-dihydroxyhexanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
-60 °C

実験手順

To the crude tert-butyl 6-triphenylmethyloxy-5-hydroxy-3-oxohexanoate was added 150 mL of THF followed by 15 mL of MeOH and was chilled to −60° C. 26 mL of MDEB (50% solution in THF) was added over a period of 20 minutes and stirring was continued for a further 30 minutes. The reaction mixture was cooled to −80° C. and 5 g of sodium borohydride was added in portions and the after completion of addition the reaction mixture was stirred for 5 hours at −78° C. Acetic acid was added to adjust the pH to 7 and water was added. The aqueous layer was extracted using EtOAC, washed with brine, dried and concentrated to give the title compound which was used as such for the next step.

後処理

  1. temperatureThe reaction mixture was cooled to −80° C.
  2. additionthe after completion of addition the reaction mixture
  3. stirringwas stirred for 5 hours at −78° C
  4. additionwas added
  5. extractionThe aqueous layer was extracted
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-9ab2539a0287423d8375aed3b4dd3da7
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07301046B2

反応ノート

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