Hydrochloric Acid → HCID 18324235, compound

HRID 1251610Notes

Reaction equation

HRID 1251610 reaction equation
[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][CH:12]([Br:17])[C:13]3=[O:16])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][CH:12]([Br:17])[CH:13]3[OH:16])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18324229HCID 18324229, compound

Product 1

HCID 18324235HCID 18324235, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a three-necked flask of 250 ml, fitted with a condenser, was added 3.55 g (12.4 mmol) of 6-phenyl-2-bromo-1-indanone, 100 ml of tetrahydrofuran (THF) and 100 ml of absolute ethanol. A dark red solution was formed and 0.40 g (10 mmol) of sodiumboronhydride was added in small portions. The mixture was stirred for 15 hours at room temperature. The mixture was poured onto ice and a 5% hydrochloric acid solution was added. The water layer was extracted 3 times with ether and the combined ether layer washed 2 times with a saturated NaCl solution. The ether was evaporated under reduced pressure yielding 2.57 g (8.89 mmol) of 6-phenyl-2-bromoindanol (72%).

Workup

  1. customTo a three-necked flask of 250 ml, fitted with a condenser
  2. customA dark red solution was formed
  3. addition0.40 g (10 mmol) of sodiumboronhydride was added in small portions
  4. additionThe mixture was poured onto ice
  5. extractionThe water layer was extracted 3 times with ether
  6. washthe combined ether layer washed 2 times with a saturated NaCl solution
  7. customThe ether was evaporated under reduced pressure

Sources & evidence

ORD record
ord-43b7ed413cde4b9eafd562847bf4c66a
Source dataset
uspto-grants-2002_01
Patent number
US06342622B1

Reaction notes

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