Tetrahydrofuran → (9RS)-(1R*,8S*)-Tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol

HRID 1879346

Reaction equation

HRID 1879346 reaction equation
[CH:1]12[CH2:12][CH2:11][CH:8]([CH:9]=[CH:10]1)[C:7]1[C:2]2=[CH:3][CH:4]=[CH:5][CH:6]=1.C1C[O:16]CC1>>[C@@H:8]12[CH2:11][CH2:12][C@H:1]([CH:10]([OH:16])[CH2:9]1)[C:2]1[C:7]2=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 1389941,4-Ethanonaphthalene, 1,4-dihydro-

Product 1

HCID 86658824(9RS)-(1R*,8S*)-Tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol

Procedure

A solution of 15.8 g of tricyclo[6.2.2.02,7]dodeca-2,4,6,9-tetraene in 42 mL of THF was added to 82 mL of 1M BH3 in THF at 0° C. The reaction mixture was stirred overnight while the temperature reached rt. The reaction was quenched by addition of 40 mL of 0.3N NaOH solution followed by 134 mL of a 35% H2O2 solution. The mixture was extracted with Et2O, washed with H2O, dried over MgSO4 and concentrated in vacuo to obtain 17.7 g of the desired compound as yellow oil.

Workup

  1. customat 0° C
  2. customreached rt
  3. customThe reaction was quenched by addition of 40 mL of 0.3N NaOH solution
  4. extractionThe mixture was extracted with Et2O
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa7cddcb63d1474db2e660d091f7ac42
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Linked notes

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