methyl (3R)-3-[(2-bromo-1-oxooctyl)oxy]-tetradecanoate → (2R)-5-hexyl-4-hydroxy-2-undecyl-2,3-dihydropyran-6-one

HRID 25483

반응식

HRID 25483 반응식
Br[CH:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:3]([O:5][C@H:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:7][C:8]([O:10]C)=O)=[O:4].C([Mg]Cl)(C)(C)C>O1CCCC1>[CH2:23]([C:2]1[C:3](=[O:4])[O:5][C@H:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:7][C:8]=1[OH:10])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

참가 물질

4

반응물 2

HCID 11123443methyl (3R)-3-[(2-bromo-1-oxooctyl)oxy]-tetradecanoateHCID 178418310HCID 178418310, 화합물

생성물 1

HCID 54690023(2R)-5-hexyl-4-hydroxy-2-undecyl-2,3-dihydropyran-6-one수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

While the α-halo ester III and the reactive species generating reagent can be combined or added in any sequence, it has been found that when the reactive species generating reagent is a Grignard reagent a simultaneous addition of the α-halo ester III and the Grignard reagent is particularly preferred. For example, simultaneous addition of 13.6 mL solution of 30.7 mmol of methyl (3R)-3-[(2-bromo-1-oxooctyl)oxy]-tetradecanoate in tetrahydro-furan (THF) and 3 equivalents of tert-butyl magnesium chloride in 86 mL of THF over a one hour period to a 60° C. reaction vessel containing about 10 mL of THF solvent resulted in 97% yield (A.N., i.e., area normalized) of (6R)-3-hexyl-4-hydroxy-6-undecyl-5,6-dihydropyran-2-one when the crude product was analyzed by a gas chromatography 1 hr after the complete addition of reagents.

후처리

  1. additionadded in any sequence, it
  2. customover a one hour
  3. customto a 60° C.
  4. customreaction vessel

출처 및 근거

ORD 기록
ord-15f7ea4835ef4058bd5e2473fdec0a79
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858749B2

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