Methanol → 5-[4-(Benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7]decan-2-one

HRID 1608579Notes

Reaction equation

HRID 1608579 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[O:12])[CH2:3]1)[CH2:9]2.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.CO>C1COCC1>[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:1][C:2]23[CH2:11][CH:6]4[CH2:7][CH:8]([CH2:10][CH:4]([C:5]4=[O:12])[CH2:3]2)[CH2:9]3)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 64184IdramantoneHCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Product 1

HCID 540192495-[4-(Benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7]decan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To KH (35%; 1.38 g; 0.012 mole) in THF (20 ml) under N2 and cooled to 0° C. is added 5-hydroxytricyclo[3.3.1.13,7 ]decan-2-one (2 g; 0.012 mole) all at once. The reaction mixture is stirred for 5 min. in an ice bath and 1 hr. at room temperature. To the reaction mixture is then added 4-(benzoxazol-2-yl)benzyl bromide (3.4 g; 0.012 mole) dissolved in THF (60 ml) at a fast drip rate. A bright yellow mixture forms and the mixture is stirred overnight at room temperature. The mixture is next cooled in an ice bath, MeOH added to quench any KH and filtered. The filtercake is washed with THF and evaporated to dryness. The product is purified using a gradient flash chromatography (eluting with 10%-25% ethyl acetate/hexane) to obtain 5-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7 ]decan-2-one (m.p. 159°-160° C.) which is used directly in Step C.

Workup

  1. customat room temperature
  2. stirringA bright yellow mixture forms and the mixture is stirred overnight at room temperature
  3. temperatureThe mixture is next cooled in an ice bath
  4. customto quench any KH
  5. filtrationfiltered
  6. washThe filtercake is washed with THF
  7. customevaporated to dryness
  8. customThe product is purified
  9. washa gradient flash chromatography (eluting with 10%-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f0f439dc1bdf4eb7981f648499c8f23b
Source dataset
uspto-grants-1995_03
Patent number
US05395846

Reaction notes

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