HCID 15137057, compound → HCID 67958391, compound

HRID 527630Notes

Reaction equation

HRID 527630 reaction equation
[OH:1][C:2]1[C:3]([CH2:12][C:13]([CH3:15])=[CH2:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1.C(OCC)(=O)C>[OH:6][CH2:5][C:4]1[C:3]([CH2:12][C:13]([CH3:15])=[CH2:14])=[C:2]([OH:1])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 15137057HCID 15137057, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 67958391HCID 67958391, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-hydroxy-2-(2-methylallyl)benzoate (Intermediate 168, 410 mg, 1.99 mmol) was dissolved in tetrahydrofuran (5 ml) to give a colourless solution. The reaction mixture was cooled at 0° C. A solution of LiAlH4 2M in THF (1.09 ml, 2.19 mmol) was added dropwise and the reaction mixture was stirred at 0° C. for 30 min. After this time the reaction mixture was poured into ice and diluted with 60 ml of ethyl acetate. Phases were separated, the organic phase was dried over Na2SO4 and evaporated under vacuum to afford the title compound (360 mg) as a colorless oil.

Workup

  1. customto give a colourless solution
  2. additionAfter this time the reaction mixture was poured into ice
  3. customPhases were separated
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-4b271cca3250450fb5ca0854421cd682
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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