Aluminium lithium hydride → (3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-5-bromophenyl)methanol

HRID 332659Notes

Reaction equation

HRID 332659 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[C:29]([Br:31])[CH:30]=1)[C:18](OCC1C=CC=CC=1)=[O:19].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:18][OH:19])[CH:28]=[C:29]([Br:31])[CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71093165Benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate

Product 1

HCID 71093288(3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-5-bromophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate in tetrahydrofuran (30 mL) at −78° C., was added a solution of lithium aluminium hydride in THF (2.0 M, 3.3 mL, 6.60 mmol). The reaction mixture was stirred for 4 hours, then quenched with water (0.25 mL), 2 M sodium hydroxide (0.25 mL) and water (0.75 mL). The coolant was removed and ethyl acetate and magnesium sulphate was added, and the mixture stirred at room temperature for 20 minutes. The suspension was filtered, washed with ethyl acetate, and the filtrate was concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-17% ethyl acetate in iso-hexane to afford the title compound as a 10:7 ratio of product to starting material (1.69 g, 73%).

Workup

  1. customquenched with water (0.25 mL), 2 M sodium hydroxide (0.25 mL) and water (0.75 mL)
  2. customThe coolant was removed
  3. additionethyl acetate and magnesium sulphate was added
  4. stirringthe mixture stirred at room temperature for 20 minutes
  5. filtrationThe suspension was filtered
  6. washwashed with ethyl acetate
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe crude material was purified by silica gel chromatography
  9. washeluting with 0-17% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-e554c44202804fbfb7fbcdb4b1c0e0ba
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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