Sulfuryl chloride → HCID 21864949, compound

HRID 131163Notes

Reaction equation

HRID 131163 reaction equation
[C:1]([C:3]1[C:4]([OH:13])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].S(Cl)([Cl:17])(=O)=O>C(#N)C>[Cl:17][C:12]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([OH:13])[C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 21864957HCID 21864957, compound

Product 1

HCID 21864949HCID 21864949, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 100 mL round-bottom flask was placed 5,6,7,8-tetrahydro-3-cyano-2-naphthol (1.0 g, 5.77 mmol, 1 eq, from Method II-2) in 20 mL of dry acetonitrile under argon. Sulfuryl chloride (6.09 mL, 28.85 mmol, 5.0 eq) was added dropwise. The reaction was stirred at rt for 18 h. The reaction mixture was concentrated and purified on silica gel (flash column chromatography) eluting with 20% ethyl acetate-hexane. A 1:1 diastereomeric mixture of 4-Chloro-3-hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile and 1-Chloro-3-hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile was obtained as a yellow liquid (887 mg, 66.6%, isomer ratio:1:1). 1H-NMR (CD3CN) δ 7.81 (s, 1H), 3.24 (m, 1H), 2.66 (m, 1H), 2.33 (m, 1H), 2.07(m, 2H), 1.88 (m, 2H), 1.43 (m, 1H). GC-MS (M+=207)

Workup

  1. customIn a 100 mL round-bottom flask was placed
  2. concentrationThe reaction mixture was concentrated
  3. custompurified on silica gel (flash column chromatography)
  4. washeluting with 20% ethyl acetate-hexane
  5. additionA 1:1 diastereomeric mixture of 4-Chloro-3-hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile

Sources & evidence

ORD record
ord-d9b204dde6334a5c99ee6c4577175edc
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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