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

HRID 854660Notes

Reaction equation

HRID 854660 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-014838ca5de44c33ba1481d57f42e7d1
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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