Methanol → 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol

HRID 1981198Notes

Reaction equation

HRID 1981198 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][C:17](O)=[O:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].B(F)(F)F.CCOCC.CO>O1CCCC1>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][CH2:17][OH:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 1266909110,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

Product 1

HCID 1852151710,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 446.4 g of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid in 2.2 l of tetrahydrofuran, stirred under argon and cooled with ice-water, is treated portionwise with 87.0 g of sodium borohydride. The mixture is stirred for 30 minutes and subsequently a solution of 290 ml of freshly distilled boron trifluoride etherate in 300 ml of dry tetrahydrofuran is added dropwise thereto over a period of 90 minutes at a temperature of 10°. The mixture is stirred at 0° for 1 hour and at room temperature for 16 hours, cooled to 0° and treated dropwise over a period of 30 minutes with 400 ml of methanol. The mixture is stirred further at 0° for 15 minutes and at room temperature for 15 minutes and the solution is subsequently evaporated in vacuo. The residue is poured into a mixture of ice and 1 l of water, extracted three times with 2 l of ether each time and the organic extracts are washed successively with 1 l of 1.5N hydrochloric acid, with 1 l of 1.5N potassium bicarbonate solution and with 1 l of water. The organic phases are combined, dried over magnesium sulfate and evaporated. There is obtained 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol in the form of an oil which crystallizes slowly upon standing.

Workup

  1. waitover a period of 90 minutes at a temperature of 10°
  2. stirringThe mixture is stirred at 0° for 1 hour and at room temperature for 16 hours
  3. temperaturecooled to 0°
  4. stirringThe mixture is stirred further at 0° for 15 minutes and at room temperature for 15 minutes
  5. customthe solution is subsequently evaporated in vacuo
  6. additionThe residue is poured into a mixture of ice and 1 l of water
  7. extractionextracted three times with 2 l of ether each time
  8. washthe organic extracts are washed successively with 1 l of 1.5N hydrochloric acid, with 1 l of 1.5N potassium bicarbonate solution and with 1 l of water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-e127d9e8c35340d9912f03643f4c69a7
Source dataset
uspto-grants-1985_04
Patent number
US04513002

Reaction notes

Loading…