Hydrochloric Acid → Tert-butyl (cis-3-hydroxymethyl-cyclohexylmethoxy)acetate

HRID 854660노트

반응식

HRID 854660 반응식
COC[O:4][CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([CH2:12][O:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7]1.Cl.[Na+].[Cl-].O>O1CCCC1.C(OC)(C)(C)C>[OH:4][CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([CH2:12][O:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 86597946Tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]acetate

생성물 1

HCID 71016892Tert-butyl (cis-3-hydroxymethyl-cyclohexylmethoxy)acetate수율 37%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

실험 절차

1.9 g of tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]-acetate are dissolved in 10 ml of tetrahydrofuran, 5 ml of conc. HCl are added and the mixture is stirred at room temperature for 2 h. 10 ml of sat. NaCl solution, 10 ml of water and 30 ml of methyl tert-butyl ether are then added, the phases are separated and the aqueous phase is extracted with methyl tert-butyl ether. The combined organic phases are dried over MgSO4 and concentrated. Flash chromatography on silica gel (heptane/ethyl acetate 3/1) gives 600 mg of tert-butyl (cis-3-hydroxymethyl-cyclohexylmethoxy)acetate as a colorless oil (TLC (heptane/ethyl acetate 2/1): Rf, starting material=0.68, Rf, product=0.18). 260 mg of this are dissolved in 5 ml of dimethylformamide, and 170 mg of tert-butyidimethylsilyl chloride are added. The solution is then cooled to 0° C., and 160 mg of imidazole are added. The solution is stirred at room temperature for 15 h, and 20 ml of sat. NaCl solution, 10 ml of water and 30 ml of methyl tert-butyl ether are then added. The phases are separated and the organic phase is washed with sat. NaCl solution, dried over MgSO4 and concentrated. This gives 350 mg of tert-butyl [cis-3-(tert-butyldimethyl-silanyloxymethyl)cyclohexylmethoxy]acetate as a colorless oil.

후처리

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with methyl tert-butyl ether
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-014838ca5de44c33ba1481d57f42e7d1
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259177B2

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