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Water → Tert-butyl 2-[cis-3-hydroxymethylcyclohexylmethoxy]-2-methylpropionate

HRID 854663
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HRID 854663 반응식
[Si]([O:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:16][O:17][C:18]([CH3:27])([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11]1)(C(C)(C)C)(C)C.O.CC(OC)(C)C>C1COCC1>[OH:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:16][O:17][C:18]([CH3:27])([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11]1
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참가 물질

5

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HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 131726568Tert-butyl 2-[cis-3-(tert-butyldimethylsilanyloxymethyl)cyclohexylmethoxy]-2-methylpropionate2회

생성물 1

HCID 57682955Tert-butyl 2-[cis-3-hydroxymethylcyclohexylmethoxy]-2-methylpropionate수율 45.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

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온도
60 °C

실험 절차

4.5 g of tert-butyl 2-[cis-3-(tert-butyidimethylsilanyloxymethyl)cyclohexyl-methoxy]-2-methylpropionate (synthesis analogously to tert-butyl 2-[cis-3-(tert-butyldimethylsilanyloxymethyl)cyclohexylmethoxy]-2-methylpropionate in Example 55) are dissolved in 85 ml of THF, 2.24 g of TBAF trihydrate are added and the mixture is stirred at 60° C. for 90 min. Water and MTBE are added, the phases are separated and the organic phase is dried over MgSO4 and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate 1:1), which gives 1.45 g of tert-butyl 2-[cis-3-hydroxymethylcyclohexylmethoxy]-2-methylpropionate. C16H30O4 (286.42), MS (ESI): 287 (MH+).

후처리

  1. customthe phases are separated
  2. dry with materialthe organic phase is dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 1:1), which

출처 및 근거

ORD 기록
ord-54b1152ae3c040b1a3eab6de9a3ac3de
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259177B2

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