HCID 11369044, compound → HCID 11183614, compound

HRID 1180789Notes

Reaction equation

HRID 1180789 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([C:15](OCC)=[O:16])[CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.O1CCCC1>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:15][OH:16])[CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11369044HCID 11369044, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11183614HCID 11183614, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g (7.63 mmol) of ethyl 1-[2-(benzyloxy)ethyl]cyclobutanecarboxylate in 20 mL of diethyl ether at 0° C. was added a 1.0 M solution of 15.9 mL (15.9 mmol) of lithium aluminum hydride in tetrahydrofuran and the contents stirred for 2 h. The reaction was quenched with 20 ml of 20% sodium hydroxide solution. After filtration, the organic phase was isolated, dried with magnesium sulfate, and concentrated under vacuum to afford 1.6 g (95%) of {1-[2-(benzyloxy)ethyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.41-7.30 (m, 5H), 4.54 (s, 2H), 3.55 (t, J=6 Hz, 2H), 2.03-1.83 (m, 8H).

Workup

  1. customThe reaction was quenched with 20 ml of 20% sodium hydroxide solution
  2. filtrationAfter filtration
  3. customthe organic phase was isolated
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ac58c270ed874157bbfdf536c5ba2f8c
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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