Dichloromethane → HCID 86668432, compound

HRID 2404216Notes

Reaction equation

[CH2:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([CH2:22][OH:23])[CH:16]=[CH:15]4)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[CH2:4]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([CH:22]=[O:23])[CH:16]=[CH:15]4)[CH2:7][CH2:6]2)[CH2:1][CH2:2][CH2:3]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 159087Triacetoxyperiodinane

HCID 669264716-(spiro[4.5]Dec-8-yloxy)-2-naphthalenemethanol

Product 1

HCID 86668432HCID 86668432, compoundYield 100.2%

Procedure

[6-(Spiro[4.5]dec-8-yloxy)-naphthalen-2-yl]-methanol (257.2 mg, 0.8285 mmol) in methylene chloride (9 mL, 100 mmol) was added Dess-Martin periodinane (0.492 g, 1.16 mmol) and was stirred at room temperature for 1 hour. After pass through si gel plug, the solvent was concentrated down to give product as a solid (256 mg, 100%). LCMS Rt=2.44 min m/z=309.56 ([M+1], 100%).

Workup

concentrationAfter pass through si gel plug, the solvent was concentrated down

Sources & evidence

ORD record: ord-4655b3fcb37b478cbb372df44e29228f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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