Hydrochloric Acid → (R)-1-[5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol

HRID 1929959Notes

Reaction equation

HRID 1929959 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([OH:17])[C:15]#[CH:16])[CH:5]=[C:4]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])[C:3]1=2.Cl>CCCCCCC.C(OC=C)(=O)C.C([O-])([O-])=O.[K+].[K+].CO>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C@H:14]([OH:17])[C:15]#[CH:16])[CH:5]=[C:4]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])[C:3]1=2

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 866125941-[5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol

Product 1

HCID 86612595(R)-1-[5,5,8,8-Tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-olYield 41%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 7904Vinyl AcetateSolventHCID 8900HeptaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
38 °C

Procedure

36 g (110 mmol) of 1-[5,5,8,8-tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol (Example 2b) are dissolved in 75 mL of heptane and 10.2 ml of vinyl acetate. 7.26 g of enzyme PS30 are added, and the reaction medium is stirred and heated to 38° C. After 72 hours, the reaction medium is filtered and concentrated under reduced pressure. Two products are separated out by chromatography: 1-[5,5,8,8-tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol (R)-acetate and (S)-1-[5,5,8,8-tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol, which will be used for Example 5. 18 g (48 mmol) of 1-[5,5,8,8-tetramethyl-4-(2-ethoxyethoxy)-5,6,7,8-tetrahydronaphth-2-yl]prop-2-yn-1-ol (R)-acetate are thus dissolved in 500 mL of a 2% solution of K2CO3 in methanol and the medium is stirred for 3 hours. The reaction medium is then treated with 0.01 N hydrochloric acid solution and extracted with ethyl acetate. The residue obtained is purified by chromatography (eluent: 8/2 heptane/EtOAc). A colorless oil is obtained (m =15 g, yield=41%).

Workup

  1. addition7.26 g of enzyme PS30 are added
  2. filtrationthe reaction medium is filtered
  3. concentrationconcentrated under reduced pressure
  4. customTwo products are separated out by chromatography
  5. stirringthe medium is stirred for 3 hours
  6. extractionextracted with ethyl acetate
  7. customThe residue obtained
  8. customis purified by chromatography (eluent: 8/2 heptane/EtOAc)
  9. customA colorless oil is obtained (m =15 g, yield=41%)

Sources & evidence

ORD record
ord-f8a49abcc01642fda738cab5456deb8c
Source dataset
uspto-grants-2012_05
Patent number
US08188106B2

Reaction notes

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