Tetrahydrofuran → HCID 70214617, compound

HRID 2268216Notes

Reaction equation

HRID 2268216 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16]([O:18][C:19]3[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=3)=[O:17])[CH:5]=[CH:4][C:3]1=2.C1COCC1.CCCCCC.[BH4-].[Na+]>O>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16]([O:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:23][OH:24])=[CH:25][CH:26]=3)=[O:17])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 4311764Sodium borohydrideHCID 57230451HCID 57230451, compound

Product 1

HCID 70214617HCID 70214617, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.1 g (8.5 mmol) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzaldehyde and 50 ml of a mixture of THF and methanol (50/50) are introduced into a round-bottomed flask. 163 mg (4.25 mmol) of sodium borohydride is added portionwise and the mixture is stirred at [lacuna] temperature for three hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate, filtered and evaporated. The solid obtained is recrystallized from a mixture of diisopropyl ether and hexane. After filtration and drying, 1.6 g (53%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzenemethanol, with a melting point of 140-50° C., are collected.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe solid obtained
  7. customis recrystallized from a mixture of diisopropyl ether and hexane
  8. filtrationAfter filtration
  9. customdrying
  10. custom1.6 g (53%) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzenemethanol, with a melting point of 140-50° C., are collected

Sources & evidence

ORD record
ord-d36a83075ffe494299370eaf8c296171
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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