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

HRID 1594450
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HRID 1594450 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매
HCID 8028Tetrahydrofuran용매2회

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온도
-60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ab2539a0287423d8375aed3b4dd3da7
출처 데이터셋
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07301046B2

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