Hydrochloric Acid → HCID 10680544, compound

HRID 2399619Notes

Reaction equation

HRID 2399619 reaction equation
[CH2:1]([O:8][CH2:9][C@:10]12[CH2:17][C@H:16]1[CH2:15][O:14]C(C)(C)[O:12][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][CH2:9][C@:10]1([CH2:11][OH:12])[CH2:17][C@H:16]1[CH2:15][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10849075HCID 10849075, compound

Product 1

HCID 10680544HCID 10680544, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5.56 g (21.1 mmol) of (1S,7 R)-1-benzyloxymethyl-4,4-dimethyl-3,5-dioxabicyclo[5,1,0]octane in 50 ml of tetrahydrofuran was mixed with 50 ml of 1N HCl and the mixture was stirred for 30 min. at 0° C. Tetrahydrofuran was evaporated off, and the residue was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated to obtain 4.08 g (18.2 mmol, 86%) of (1R,2 R)-1-benzyloxymethyl-2-hydroxymethyl cyclopropane-1-methanol. Colorless oil; 1H-NMR(CDCl3) δ: 0.41 (t, J=10.8 Hz, 1H), 0.66 (dd, J=5.4, 8.7 Hz, 1H), 1.32 (m, 1H), 3.25-3.4 (m, 4H) 3.60 (dd, J=1.7, 9.6 Hz, 1H), 4.06 (m, 1H), 4.22 (d, J=7.2 Hz, 1H), 4.27 (d, J=7.2 Hz, 1H), 4.56 (s, 2H), 7.34 (m, 5H); FD MASS, m/z 223(MH+).

Workup

  1. customTetrahydrofuran was evaporated off
  2. extractionthe residue was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-7a332f9c9eca47088ac3836ef1ea6d31
Source dataset
uspto-grants-1995_09
Patent number
US05449840

Reaction notes

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