Ethyl formate → HCID 18615023, compound

HRID 1265251Notes

Reaction equation

HRID 1265251 reaction equation
[Na].[OH:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.[CH:20](OCC)=[O:21]>Cl>[OH:21][CH:20]1[CH2:18][C:17](=[O:19])[C:4]2[C:3](=[CH:12][C:11]3[C:10]([CH3:13])([CH3:14])[CH2:9][CH2:8][C:7]([CH3:16])([CH3:15])[C:6]=3[CH:5]=2)[O:2]1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketoneHCID 5360545Sodium

Product 1

HCID 18615023HCID 18615023, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
35 °C

Procedure

A 200-mL round bottom flask was flame dried under nitrogen and charged with sodium metal (3.2 g, 140 mmol). A solution of 1-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)ethanone (15 g, 61.0 mmol) in ethyl formate (350 mL) was added dropwise over 1 h. The resulting yellow solution was stirred at 35° C. for 4 h. The mixture was cooled to 25° C. solution, diluted with 1N HCl (20 mL) and extracted with ether. The extracts were washed with water, brine, and dried over MgSO4. The extracts were concentrated under vacuum to give 2-hydroxy-6,6,9,9-tetramethyl-2,3,6,7,8,9-hexahydrobenzo[g]chromen-4-one: 1H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H, ArH), 6.9 (s, 1H, ArH), 5,85 (t, 1H, CH), 3.32 (br s, 1H, OH), 2.9 (dd, 2H, CH2), 1.67 (s, 4H, 2CH2), 1.27 (s, 12H, 4CH3).

Workup

  1. temperatureA 200-mL round bottom flask was flame
  2. customdried under nitrogen
  3. temperatureThe mixture was cooled to 25° C. solution
  4. extractionextracted with ether
  5. washThe extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationThe extracts were concentrated under vacuum

Sources & evidence

ORD record
ord-7c7bf36e9e4c4b22bd6b2f473ffc3585
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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