HCID 3818598, compound → 2H-1-Benzopyran, 2,2-dimethyl-6,7-bis(phenylmethoxy)-

HRID 986839Notes

Reaction equation

HRID 986839 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:15][C:14]([CH3:28])([CH3:27])[CH2:13][C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.O.[Pd](Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:15][C:14]([CH3:28])([CH3:27])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 3818598HCID 3818598, compoundHCID 4311764Sodium borohydride

Product 1

HCID 1839612H-1-Benzopyran, 2,2-dimethyl-6,7-bis(phenylmethoxy)-Yield 81%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7.8 g (20 millimoles) of 6,7-dibenzyloxy-2,2-dimethyl-4-chromanone are dissolved in 100 ml of a 1:1 mixture of tetrahydrofurane and water, whereupon 5.3 g (30 millimole) of palladium chloride and 8.31 g (220 millimoles) of sodium tetrahydroborate are added. The reaction mixture is stirred at 0° C. for 3 hours, filtered, and the filtrate is extracted three times with 100 ml of ether each. The ether extracts are evaporated, the residue is dissolved in 300 ml of dichloro methane and allowed to stand at 35° C. in the presence of 15 ml of pyridine and 2 g of phosphorous oxychloride for an hour. The reaction mixture is poured into 100 ml of water washed with 5% hydrochloric acid and water. The organic phase is dried and evaporated. The residue is crystallized from methanol. Thus 6 g of the desired compound are obtained, yield 81%. Mp.: 50°-51° C.

Workup

  1. additionare added
  2. filtrationfiltered
  3. extractionthe filtrate is extracted three times with 100 ml of ether each
  4. customThe ether extracts are evaporated
  5. dissolutionthe residue is dissolved in 300 ml of dichloro methane
  6. waitto stand at 35° C. in the presence of 15 ml of pyridine and 2 g of phosphorous oxychloride for an hour
  7. additionThe reaction mixture is poured into 100 ml of water
  8. washwashed with 5% hydrochloric acid and water
  9. customThe organic phase is dried
  10. customevaporated
  11. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-689c556393a0494dbddbf9112a643427
Source dataset
uspto-grants-1987_12
Patent number
US04716238

Reaction notes

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