Acetaldehyde → HCID 13833724, compound

HRID 460307Notes

Reaction equation

HRID 460307 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[Li]CCCC.[CH:18](=[O:20])[CH3:19].Cl>C1COCC1>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[C:2]([CH:18]([OH:20])[CH3:19])[CH:3]=[CH:4][C:5]=2[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuranHCID 178418339Butyllithium

Product 1

HCID 13833724HCID 13833724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (example 1f) (3.50 g, 15.4 mmol) in dry THF (20 mL) at −78° C., under argon, was added dropwise n-BuLi (1.6 M in hexane, 23.1 mmol, 14.4 mL). The mixture was stirred for 2 hours then acetaldehyde (0.95 mL) was added and the mixture was slowly warmed up to room temperature and stirred overnight at room temperature. 1N HCl was added and the solution extracted with ethyl acetate and the organic extract was dried (MgSO4), filtered and evaporated to give 3.3 g of 1-(3,3-dimethyl-2,3-dihydro-benzofuran5-yl)-ethanol. 1H NMR (300 MHz; CDCl3): δ 1.35 (s, 6H), 1.49 (d, J=6.5 Hz, 3H), 4.24 (s, 2H), 4.86 (q, J=6.5 Hz, 1H), 6.75 (d, J=8.2 Hz, 3H), 7.10–7.15 (m, 2H).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionthe solution extracted with ethyl acetate
  3. extractionthe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9cfb28248466494786fc617885d062d8
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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