Hydrochloric Acid → HCID 178492629, compound

HRID 1490141Notes

Reaction equation

HRID 1490141 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C@H:14]2[CH2:17][C@H:16]([C:18](OCC)=[O:19])[CH2:15]2)=[CH:11][CH:10]=1.O.Cl>CCOCC>[CH3:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C@H:14]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH2:15]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178472522HCID 178472522, compound

Product 1

HCID 178492629HCID 178492629, compoundYield 121%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of lithium aluminum hydride (389 mg, 10.0 mmol) in ether (413 ml) was added a solution of ethyl trans-3-(4-methoxyphenoxy)cyclobutanecarboxylate (1.97 g, 7.9 mmol) in ether (10 ml) at 0° C. and the mixture stirred for 1 h at room temperature. Water (3 ml) was carefully added to the reaction mixture at 0° C. and the whole allowed to warm to room temperature. 1 N aqueous hydrochloric acid (50 ml) was added, the ether phase separated and the aqueous phase extracted with ethyl acetate (100 ml). The combined organic phase was dried (MgSO4) and concentrated in vacuo to provide 1.99 g (quant.) of {trans-3-(4-methoxyphenoxy)-cyclobutyl }methanol as white solids. The product was used without further purification: 1H NMR δ6.88-6.70 (m, 4H), 4.75-4.62 (m, 1H), 3.76 (s, 3H), 3.71 (d, J=6.6 Hz, 2H), 2.62-2.46 (m, 1H), 2.35-2.28 (m, 4H), 1.59 (s, 1H).

Workup

  1. temperatureto warm to room temperature
  2. customthe ether phase separated
  3. extractionthe aqueous phase extracted with ethyl acetate (100 ml)
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-214301a95bc249cc96131b8813ba29d4
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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