Acetic Acid → HCID 118511097, compound

HRID 1478159Notes

Reaction equation

HRID 1478159 reaction equation
[O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][O:10][C:9]3=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.C(O)(=O)C.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][O:10][CH:9]3[OH:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 14487Diisobutylaluminum hydrideHCID 13671287HCID 13671287, compound

Product 1

HCID 118511097HCID 118511097, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

1,4,10-Trioxadispiro[4.2.4.2]tetradecan-9-one (880 mg, 4.15 mmol) in toluene (30 mL), under nitrogen, was cooled to −78° C. and treated with 1M DIBAL-H (1M in toluene) (4.56 mL, 4.56 mmol). The reaction mixture was stirred at −78° C. for 2 hours. The resulting mixture was treated with 10% aqueous acetic acid solution (18 mL)/ice 60 g) and stirred for 5 mins with chloroform (150 mL). The aqueous was separated and extracted with chloroform (×3) and the combined organic extracts were dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford the title compound;

Workup

  1. customThe aqueous was separated
  2. extractionextracted with chloroform (×3)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fdd79c38dbf94f888ac891345db36bd6
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

Loading…